Methanol → HCID 91349945, compound

HRID 1745018Notes

Reaction equation

HRID 1745018 reaction equation
C([O:4][CH2:5][CH2:6][NH:7][C:8]([C@@H:10]1[CH2:14][C:13](=[N:15][O:16][CH3:17])[CH2:12][N:11]1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=[O:19])=[O:9])(=O)C.[OH-].[Na+].CO>C1COCC1>[C:23]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:22]=[CH:21][C:20]([C:18]([N:11]2[CH2:12][C:13](=[N:15][O:16][CH3:17])[CH2:14][C@H:10]2[C:8]([NH:7][CH2:6][CH2:5][OH:4])=[O:9])=[O:19])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 131725402HCID 131725402, compound

Product 1

HCID 91349945HCID 91349945, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution was made containing the side-chain protected compound from the previous step, e.g. 2-({[(2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)pyrrolidinyl]carbonyl}amino)ethyl acetate (450 mg, 10.6 mmol) in THF (10 ml). An aqueous solution (10 ml) of sodium hydroxide (75 mg, 19 mmol) with methanol (5 ml) was added and the reaction stirred at room temperature for three hours. The solvent was removed in vacuo and the crude purified by column chromatography using THF (100%) to give the expected final product, e.g. (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N-(2-hydroxyethyl)-4-(methoxyimino)-2-pyrrolidinecarboxamide (300 mg, 75%) as a white solid.

Workup

  1. additionA solution was made containing the side-chain
  2. customThe solvent was removed in vacuo
  3. customthe crude purified by column chromatography

Sources & evidence

ORD record
ord-522e0f73fdc34373b65a1df722489ecd
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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