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0344327892
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note
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Our preliminary studies (see: Coltart, D. M., Ph.D. Thesis, University of Alberta, 2000) were based on thiophenolic and 1-phenyl-2-mercaptoethyl systems exemplified by i and ii. Work on the former was stopped when similar studies by Dawson and Offer (ref 5r) were published. A noteworthy feature of ii (and 2.1) is that the mercapto group ultimately released is an alkyl thiol and, as such, is more nucleophilic than an aryl thiol (cf. i).
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31
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0345190342
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PCT Int. Appl. WO 2002/20557
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The possibility of preparing compounds of type 2.1 by reductive amination or by halide displacement (cf. the present method) is shown in a generic scheme in two patents: (a) Botti, P.; Bradburne, J. A.; Kent, S. B. H.; Low, D. W. PCT Int. Appl. WO 2002/20557.
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0344759921
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PCT Int. Appl. WO 2002/20034
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(b) Kent, S. B. H.; Botti, P.; Low, D. W.; Bradburne, J. A.; Hunter, C. L., Chen, S.-Y.; Cressman, S.; Kochendoerfer, G. PCT Int. Appl. WO 2002/20034.
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Kochendoerfer, G.8
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Van Der Gen, A.4
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36
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0345622527
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note
-
2, rt, 6 h) and less efficient (64% of 4.3) than the route of Scheme 4.
-
-
-
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38
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0033548208
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0345190341
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note
-
19F δ -69.6 and -69.4 ppm).
-
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45
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0000496038
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0344327891
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note
-
2O-DMAP-t-BuOH (ref 22) gave partially racemized material.
-
-
-
-
47
-
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0345622526
-
-
note
-
(b) Transesterification with tert-butyl acetate (ref 23) was very slow and proceeded in poor yield.
-
-
-
-
50
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0028006935
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84982064001
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-
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0345190340
-
-
note
-
(b) L-Alanine tert-butyl ester is commercially available.
-
-
-
-
54
-
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0344327890
-
-
note
-
3OD, 100 MHz) δ 41.5 (t'), 44.3 (t'), 128.5 (d'), 128.7 (d'), 129.6 (d'), 139.4 (s'), 167.1 (s').
-
-
-
-
56
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0022226409
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57
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0345190339
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note
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2NEt).
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0032795406
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