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

HRID 2394155
ノート
印刷プレビュー

反応式

HRID 2394155 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][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]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][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 3939Lithium HydroxideHCID 677093875(S)-[1(S)-(Boc-Amino)-2-cyclohexylethyl]-3(R)-[(2,3,4-trimethoxyphenyl)-methyl]dihydrofuran-2-(3H)-one

生成物 1

HCID 228763975(S)-(Boc-Amino)-4(S)-hydroxy-6-cyclohexyl-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 600 mg (1.22 mmol) of 5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]-3(R)-[(2,3,4-trimethoxyphenyl)methyl]dihydrofuran-2-(3H)-one in 20 ml of dimethoxyethane and 9.9 ml of water is treated, at RT, with 4.9 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 and diluted with 60 ml of sat. ammonium chloride solution and 5 ml of a 10% citric acid solution (both being cold); 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. IR(CH2 Cl2) inter alia: 3431, 1710, 1602, 1495, 1165 and 1100 cm-1. FAB-MS (M+H)+ =510. HPLC tRet =16.13 min (gradient II).

後処理

  1. customIt is then transferred to a separating funnel
  2. extractionthis mixture is 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
  8. customtRet =16.13 min (gradient II)

出典と根拠

ORDレコード
ord-59c1e2ee95274749b5366c3756bd5b90
出典データセット
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05807891

反応ノート

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