Water → HCID 67505690, compound

HRID 2384040Notes

Reaction equation

HRID 2384040 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11](=[O:35])[NH:12][C@H:13]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH2:14][C@H:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:16])[N:8]=[C:7](Cl)[N:6]=1)=[O:4].[CH3:37][O-:38].[Na+].O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11](=[O:35])[NH:12][C@H:13]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH2:14][C@H:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:16])[N:8]=[C:7]([O:38][CH3:37])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 59608137HCID 59608137, compound

Product 1

HCID 67505690HCID 67505690, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-butylcarbamoyl)-2-chloro-pyrimidine-4-carboxylic acid methyl ester (74 mg, 0.145 mmol, from Example 42-1) in THF (5 mL) is added sodium methoxide (47 mg, 0.218 mmol) and the mixture is stirred at room temperature for 18 hours. Water is added and the mixture is extracted with EtOAc. The organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure to give 6-((1S,3R)-1-biphenyl-4-ylmethyl-3-ethoxycarbonyl-butylcarbamoyl)-2-methoxy-pyrimidine-4-carboxylic acid methyl ester.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic phase is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-176660f0a6c54093b98015e8a78bef64
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

Loading…