Lithium Hydroxide → 5(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,3,4-trimethoxyphenyl)-methyl]hexanoic acid

HRID 2394135ノート

反応式

HRID 2394135 の反応式
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[C:25]=2[O:34][CH3:35])[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:36].[Li+]>C(COC)OC.O.[Cl-].[NH4+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[C:25]=1[O:34][CH3:35])[C:20]([OH:36])=[O:22])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

参加物

7

反応物 2

HCID 3939Lithium HydroxideHCID 152958925(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,3,4-trimethoxyphenyl)methyl]dihydrofuran-2-(3H)-one

生成物 1

HCID 228742855(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(2,3,4-trimethoxyphenyl)-methyl]hexanoic acid

試薬・触媒・溶媒 4

HCID 311Citric Acid溶媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 25517Ammonium Chloride溶媒

実験手順

A solution of 1.354 g (2.685 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2,3,4-trimethoxyphenyl)methyl]dihydrofuran-2-(3H)-one in 43.36 ml of dimethoxyethane and 21.86 ml of water is treated, at RT, with 10.74 ml of a 1M solution of lithium hydroxide in water, and this reaction mixture is stirred for 2 h. It is then transferred to a separating funnel, diluted with 132 ml of sat. ammonium chloride solution and 11 ml of a 10% citric acid solution (both cold), and this mixture is then extracted with ethyl acetate and a little THF. The title compound, which is dried under HV and subjected to further processing without being purified, is obtained after washing the organic phase with (cold) saline and drying it over sodium sulfate. TLC Rf (C)=0.03. MS (M-H2O)+ =485.

後処理

  1. customIt is then transferred to a separating funnel
  2. extractionis then extracted with ethyl acetate
  3. dry with materialThe title compound, which is dried under HV
  4. customwithout being purified
  5. customis obtained
  6. washafter washing the organic phase with (cold) saline
  7. dry with materialdrying it over sodium sulfate

出典と根拠

ORDレコード
ord-c94b377a3d1e4705bc6b5b074c82a401
出典データセット
uspto-grants-1998_09
特許番号
US05807891

反応ノート

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