Lithium Hydroxide → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

HRID 1377158노트

반응식

HRID 1377158 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][CH:27]=[CH:26][CH:25]=2)[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.[OH-:30].[Li+].C[O:33]CCOC>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][CH:27]=[CH:26][CH:25]=1)[C:20]([OH:22])=[O:33])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:30]

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 117320045(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-phenylmethyldihydrofuran-2-(3H)one

생성물 1

HCID 99791245(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 17.6 g of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-phenylmethyldihydrofuran-2-(3H)one in 710 ml of ethylene glycol dimethyl ether and 352 ml of water is treated dropwise, at 20° C. and within the space of 10 min, with 176 ml of a 1M lithium hydroxide solution. After that, the reaction mixture is stirred at RT for 1.5 h, and the solvent is then evaporated off. The residue is poured onto 1 of cold 10% citric acid, and this acidic solution is extracted three times with 800 ml of ethyl acetate on each occasion. The combined extracts are washed first with 800 ml of water and then with 800 ml of saline. After the organic solution has been dried over sodium sulfate, the solvent is distilled off. The crude title compound is employed in the next stage without any further purification. FAB-MS (M+H)+ =414.

후처리

  1. customthe solvent is then evaporated off
  2. additionThe residue is poured onto 1 of cold 10% citric acid
  3. extractionthis acidic solution is extracted three times with 800 ml of ethyl acetate on each occasion
  4. washThe combined extracts are washed first with 800 ml of water
  5. dry with materialAfter the organic solution has been dried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. customThe crude title compound is employed in the next stage without any further purification

출처 및 근거

ORD 기록
ord-0e53222c7b024327a44b26e4b9e22540
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663200

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