2-Naphthoyl chloride → L-Proline, 1-(3-((4-amino-2-((2-naphthalenylcarbonyl)amino)-1,4-dioxobutyl)amino)-2-hydroxy-4-phenylbutyl)-, 1,1-dimethylethyl ester, (2R-(2R*,3S*(S*)))-

HRID 742842

反応式

HRID 742842 の反応式
[C:1]([O:5][C:6](=[O:32])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:31])[C@@H:14]([NH:22][C:23](=[O:30])[C@H:24]([CH2:26][C:27](=[O:29])[NH2:28])[NH2:25])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[C:43](Cl)=[O:44].C(N(C(C)C)CC)(C)C>ClCCl>[C:1]([O:5][C:6](=[O:32])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:31])[C@@H:14]([NH:22][C:23](=[O:30])[C@H:24]([CH2:26][C:27](=[O:29])[NH2:28])[NH:25][C:43]([C:34]1[CH:35]=[CH:36][C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=1)=[O:44])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 752462-Naphthoyl chlorideHCID 81531DiisopropylethylamineHCID 70041604N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester

生成物 1

HCID 451725L-Proline, 1-(3-((4-amino-2-((2-naphthalenylcarbonyl)amino)-1,4-dioxobutyl)amino)-2-hydroxy-4-phenylbutyl)-, 1,1-dimethylethyl ester, (2R-(2R*,3S*(S*)))-収率 64.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 249 mg of N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester, 106 mg of 2-naphthoyl chloride and 72 mg of diisopropylethylamine in 10 ml of dry dichloromethane was stirred at 20° C. for 20 hours. The gelatinous reaction mixture was partitioned between dichloromethane and water. The organic phase was evaporated and the resulting oil was crystallized from ethyl acetate/n-hexane to give 215 mg of N-[2(R)-hydroxy-3(S)-[[N-(2-naphthoyl)-L-asparaginyl]amino]-4-phenylbutyl]-L-proline tert.butyl ester, as a white solid; MS: m/e 603 [M+H]+.

後処理

  1. customThe gelatinous reaction mixture was partitioned between dichloromethane and water
  2. customThe organic phase was evaporated
  3. customthe resulting oil was crystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-cfe64efaa06e4dcdae8ff5beeb250f49
出典データセット
uspto-grants-1996_09
特許番号
US05554756

関連ノート

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