Methanol → HCID 11466046, compound

HRID 1592982Notes

Reaction equation

HRID 1592982 reaction equation
[C:1]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]([CH2:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([O:30][CH2:31][CH3:32])[C:26]([O:28]C)=[O:27])=[CH:20][CH:19]=3)[CH:15]=[CH:16][CH:17]=2)[CH3:10])=[O:8])=[CH:3][CH:2]=1.O.[OH-].[Li+].O.CO>C1COCC1>[C:1]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]([CH2:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([O:30][CH2:31][CH3:32])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=3)[CH:15]=[CH:16][CH:17]=2)[CH3:10])=[O:8])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 86588728HCID 86588728, compound

Product 1

HCID 11466046HCID 11466046, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

360 mg (0.7 mmol) of methyl (S)-3-(3′-{[(1-biphenyl-4-ylmethanoyl)methylamino]methyl}biphenyl-4-yl)-2-ethoxypropionate in 10 ml of THF are introduced into a round-bottomed flask. 60 mg (1.4 mmol) of lithium hydroxide monohydrate, 1 ml of water and 1 ml of methanol are added and the mixture is stirred for 4 hours. The reaction medium is poured into water, acidified to pH 1, extracted with ethyl acetate, the organic phase decanted off, dried over magnesium sulphate and evaporated off. The residue obtained is purified by chromatography on a silica column eluted with a heptane and ethyl acetate (50/50) mixture and 280 mg (80%) of (S)-3-(3′-{[(1-biphenyl-4-ylmethanoyl)methylamino]methyl}biphenyl-4-yl)-2-ethoxypropionic acid are obtained in the form of an amorphous white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase decanted off
  3. dry with materialdried over magnesium sulphate
  4. customevaporated off
  5. customThe residue obtained
  6. customis purified by chromatography on a silica column
  7. washeluted with a heptane and ethyl acetate (50/50) mixture and 280 mg (80%) of (S)-3-(3′-{[(1-biphenyl-4-ylmethanoyl)methylamino]methyl}biphenyl-4-yl)-2-ethoxypropionic acid
  8. customare obtained in the form of an amorphous white solid

Sources & evidence

ORD record
ord-29fceec1f5bb44fbbda58d9992aef7ce
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

Loading…