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

HRID 51192

反応式

HRID 51192 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-69c8cfbd21774ea0b20386ad05cc23fc
出典データセット
uspto-grants-2004_03
特許番号
US06713603B2

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