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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2394155
[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]
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Komponenten

7

Edukt 2

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

Produkt 1

HCID 228763975(S)-(Boc-Amino)-4(S)-hydroxy-6-cyclohexyl-2(R)-[(2,3,4-trimethoxyphenyl)methyl]hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 311Citric AcidLösungsmittel
HCID 962
Water
Lösungsmittel
2×
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-59c1e2ee95274749b5366c3756bd5b90
Quelldatensatz
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05807891

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