Water → HCID 67505690, compound

HRID 1469619Notes

Reaction equation

HRID 1469619 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-c17e3519496048d5bd96d373d758ac58
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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