1,1'-(Diazomethylene)bis(benzene) → N-tert-butoxycarbonyl-trans-4-hydroxy-L-proline diphenylmethyl ester

HRID 51192

반응식

HRID 51192 반응식
[C:1]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17]1([C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N+]=[N-])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)(=O)C>[C:17]1([CH:23]([O:11][C:10](=[O:12])[C@@H:9]2[CH2:13][C@@H:14]([OH:16])[CH2:15][N:8]2[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

4

반응물 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

생성물 1

HCID 21348449N-tert-butoxycarbonyl-trans-4-hydroxy-L-proline diphenylmethyl ester수율 91%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of freshly prepared diphenyldiazomethane22 (3.50 g, 18.0 mmol) in ethyl acetate (20 ml) was added N-Boc-trans-4-hydroxy-L-proline (3.25 g, 14.0 mmol) in ethyl acetate (30 ml). Nitrogen gas was slowly evolved from the solution and the intense purple colour of diphenyldiazomethane was gradually discharged. The solution was stirred at room temperature overnight using a CaCl2 guard tube. Evaporation of the solvent followed by precipitation of the product from ethyl acetate-petroleum ether b.p. 40-60° C. gave a white solid, N-tert-butoxycarbonyl-trans-4-hydroxy-L-proline diphenylmethyl ester (2a), (5.10 g, 91%), m.p. 93-95° C. (lit.9 m.p. 103-104° C.), δH (200 MHz; CDCl3) 1.22 and 1.47 (9H, 2×s, Boc rotamers), 1.95-2.50 [3H, br m, CH2(3) and OH], 3.45-3.74 [2H, br m, CH2(5)], 4.40-4.65 [2H, br m, CH(2)and CH(4)], 6.95 (1H, br s, CHPh2), 7.25-7.55 (10H, br m, phenyl CH); νmax (KBr)/cm−1 3491br (O—H), 1728s (C═O ester), 1693s (C═O urethane); m/z (ES MS) 436 (M+K+, 55%), 420 (M+Na+, 100), 415 (M+NH4+, 15), 398 (M+H+, 72); [α]D25−54.3 (C=1.0, EtOH).

후처리

  1. customEvaporation of the solvent
  2. customfollowed by precipitation of the product from ethyl acetate-petroleum ether b.p. 40-60° C.

출처 및 근거

ORD 기록
ord-69c8cfbd21774ea0b20386ad05cc23fc
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713603B2

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