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Another reason for selection of KHMDS as a standard base was the known favorable character of potassium enolates for O-alkylation, which is needed to obtain the 4-alkoxy derivatives in high purities through a subsequent in situ alkylation of the cleaved products. The study on the efficient alkylation is in progress using polymer-supported alkylating agents and will be reported elsewhere
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Another reason for selection of KHMDS as a standard base was the known favorable character of potassium enolates for O-alkylation, which is needed to obtain the 4-alkoxy derivatives in high purities through a subsequent in situ alkylation of the cleaved products. The study on the efficient alkylation is in progress using polymer-supported alkylating agents and will be reported elsewhere.
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Representative Procedure for Preparation of Compounds 9 Preparation of 2-Benzylaminobenzoate Resin (7a; X, H, R1, Ph) To a mixture of the resin 1a (X, H; 4.00 g, theoretically 3.59 mmol, prepared from Wang resin (1.00 mmol/g, and benzaldehyde (1.14 g, 10.8 mmol) in DCE (60 mL) at r.t. was added NaBH(OAc)3 (2.28 g, 10.8 mmol, The mixture was stirred at r.t. for 12 h and the resin was filtered, washed several times with CH2Cl2, DMF, MeOH, H2O, and MeOH, and dried in a vacuum oven to give 7a (4.30 g, 99, on-bead ATR-FTIR: 3365 (NH, 3025, 2922, 1680 (C=O, 1602, 1581, 1512, 1492, 1451, 1221, 1172, 1097, 822, 750, 697 cm-1. Preparation of 2-{Benzyl[3-(4-methoxyphenyl)acetyl] amino}benzoate Resin (8a; X, H, R1, Ph, R2, 4-MeOC 6H4) To a mixture of the resin 7a (X, H, R1, Ph; 1.00 g, theoretically 0.830 mmol) and 4-methoxyphen
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(a) Kafka, S.; Klkgek, A.; Polis, J.; Komrlj, J. Heterocycles 2002, 57, 1659.
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(2002)
Heterocycles
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, pp. 1659
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Kafka, S.1
Klkgek, A.2
Polis, J.3
Komrlj, J.4
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(b) Stadlbauer, W.; Laschober, R.; Lutschounig, H.; Schindler, G.; Kappe, T. Monatsh. Chem. 1992, 123, 617.
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(1992)
Monatsh. Chem
, vol.123
, pp. 617
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Stadlbauer, W.1
Laschober, R.2
Lutschounig, H.3
Schindler, G.4
Kappe, T.5
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(c) Bowman, R. E.; Grey, T. F.; Huckle, D.; Lockhart, I. M.; Wright, M. J. Chem. Soc. 1964, 3350.
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(1964)
J. Chem. Soc
, pp. 3350
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Bowman, R.E.1
Grey, T.F.2
Huckle, D.3
Lockhart, I.M.4
Wright, M.5
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