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

HRID 2394135노트

반응식

HRID 2394135 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 311Citric Acid용매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 25517Ammonium Chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c94b377a3d1e4705bc6b5b074c82a401
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05807891

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