Water → (S)-(4-Benzyloxy-phenyl)-tert-butoxycarbonylamino-acetic acid benzyl ester

HRID 1009965ノート

反応式

HRID 1009965 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C>[CH2:26]([O:11][C:10](=[O:12])[C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:9][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:15][CH:14]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11300124(S)-2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetic acid

生成物 1

HCID 57994316(S)-(4-Benzyloxy-phenyl)-tert-butoxycarbonylamino-acetic acid benzyl ester収率 184%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of (S)-tert-butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid (32.03 g, 120 mmol) in DMF (300 ml) was added potassium carbonate (35 g, 252 mmol) and benzylbromide (30 ml, 252 mmol). The reaction mixture was stirred at 50° C. under a nitrogen atmosphere for 17 h. The mixture was poured into water (1l) and extracted with EtOAc (3×600 ml). The combined organic extracts were washed with water (3×600 ml), brine (600 ml), dried over magnesium sulfate, filtered and evaporated in vacuo to yield a yellow oil (49.4 g, 92%). LCMS purity 100%, m/z 470 [M++Na]+.

後処理

  1. extractionextracted with EtOAc (3×600 ml)
  2. washThe combined organic extracts were washed with water (3×600 ml), brine (600 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-b0a54dd38a314b189200280e9cf75d18
出典データセット
uspto-grants-2011_07
特許番号
US07973181B2

反応ノート

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