Formic Acid → 2-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

HRID 2222984ノート

反応式

HRID 2222984 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:44])[C@@H:12]([NH:20][C:21](=[O:43])[CH:22]([NH:32]C(OCC2C=CC=CC=2)=O)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH3:31])[CH:24]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].C(O)=O>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:44])[C@@H:12]([NH:20][C:21](=[O:43])[CH:22]([NH2:32])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH3:31])[CH:24]=2)[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[S:8][CH:9]=1)=[O:4]

参加物

5

反応物 2

HCID 284Formic AcidHCID 866040582-{(S)-2-[2-benzyloxycarbonylamino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

生成物 1

HCID 866040592-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of 2-{(S)-2-[2-benzyloxycarbonylamino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester (1.0 g, 1.62 mmol) in methanol (40 mL) was added formic acid (4 g, 87 mmol). The solution was then degassed with nitrogen for 10 minute, followed by the addition of palladium black (1 g, 9.4 mmol). The reaction mixture was stirred at room temperature under nitrogen for 0.5 hours. The reaction mixture was filtered through a short pad of celite and the filtrate was concentrated to dryness. The residue was neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated to give crude 2-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as an off white foam (0.73 g, 93%).

後処理

  1. customThe solution was then degassed with nitrogen for 10 minute
  2. filtrationThe reaction mixture was filtered through a short pad of celite
  3. concentrationthe filtrate was concentrated to dryness
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-2e87d40d169f40b080a5ec56982b3116
出典データセット
uspto-grants-2008_05
特許番号
US07371869B2

反応ノート

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