SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 14, 2009, Pages 2242-2244

Unexpected variations in sites of lithiation of N-(2-methoxybenzyl)- pivalamide

(3) Smith, Keith a El Hiti, Gamal A a Hegazy, Amany S a

a CARDIFF UNIVERSITY (United Kingdom)

Author keywords

Dilithium intermediate; Directed lithiation; Electrophile; N (2 methoxybenzyl)pivalamide; Synthesis

Indexed keywords

2 METHOXY 3 (PIVALOYLAMINOMETHYL)BENZOIC ACID; 3 METHOXY 2 (PIVALOYLAMINOMETHYL)BENZOIC ACID; AMIDE; BENZOIC ACID DERIVATIVE; N (2 METHOXYBENZYL)PIVALAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LITHIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 69249120921 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217722 Document Type: Article

Times cited : (18)

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50
- 69249158007
- Analytical Data for Compound 2: Mp 170-171 °C (lit. 6 168-169 °C, 1H NMR (500 MHz, DMSO-d 6, δ, 7.43 (t, J, 6 Hz, exch, 1 H, NH, 7.34 (app. t, J, 8 Hz, 1 H, H-5, 7.27 (dd, J, 2, 8 Hz, 1 H, H-6, 7.19 (br d, J, 8 Hz, 1 H, H-4, 4.47 (d, J, 6 Hz, 2 H, CH2, 3.82 (s, 3 H, OCH3, 1.05 [s, 9 H, C(CH3)3] ppm. 13C NMR (125 MHz, DMSO-d6, δ, 177.5 (s, C=O, 169.7 (s, CO2H, 158.4 (s, C-3, 134.3 (s, C-2, 128.7 (d, C-5, 126.7 (s, C-1, 121.6 (d, C-6, 114.6 (d, C-4, 56.5 (q, OCH3, 38.4 [s, C(CH3)3, 35.7 (t, CH2, 27.8 [q, C(CH3)3] ppm. MS (ES, m/z, 553 (34, 2 M, Na, 531 (42, 2 M, H, 329 (32, M, MeCNNa, 304 (3, M, K, 266 100, MH
- 1.

51
- 69249106344
- Analytical Data for Compound 4: Mp 156-157 °C. 1H NMR (500 MHz, DMSO-d6, δ, 8.03 (t, J, 6 Hz, exch, 1 H, NH, 7.57 (dd, J, 2, 8 Hz, 1 H, H-6, 7.32 (dd, J, 2, 8 Hz, 1 H, H-4, 7.16 (app. t, J, 8 Hz, 1 H, H-5, 4.32 (d, J, 6 Hz, 2 H, CH2, 3.79 (s, 3 H, OCH3, 1.15 [s, 9 H, C(CH 3)3] ppm. 13C NMR (500 MHz, DMSO-d 6, d, 178.1 (s, C=O, 167.8 (s, CO2H, 157.1 (s, C-2, 134.6 (s, C-3, 131.5 (d, C-4, 129.6 (d, C-6, 126.1 (s, C-1, 123.9 (d, C-5, 62.1 (q, OCH3, 38.6 [s, C(CH3)3, 37.3 (t, CH2, 27.9 [q, C(CH3)3] ppm. MS (ES, m/z, 569 (12, 2 M, K, 553 (100, 2 M, Na, 548 (32, 2 M, NH4, 329 (25, M, MeCNNa, 304 (27, M, K, 288 (70, M, Na, 266 71, MH, HRMS
- max = 3377, 2972, 1698, 1610, 1540, 1427, 1368, 1247 cm-1.

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