Citric Acid → HCID 178483047, compound

HRID 22944Notes

Reaction equation

HRID 22944 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][N:19]=[C:18]([N:27]([CH3:29])[CH3:28])[N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([O:15][C:16]2[C:21]([C:22]([OH:24])=[O:23])=[CH:20][N:19]=[C:18]([N:27]([CH3:29])[CH3:28])[N:17]=2)[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 178469830HCID 178469830, compound

Product 1

HCID 178483047HCID 178483047, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 15 mL of ethanol was dissolved 2.675 g of N-tert-butoxycarbonyl-trans-4-[5-ethoxycarbonyl-2-(dimethylamino)pyrimidin-4-yloxy]cyclohexylamine (the compound of Reference Example 9-50 prior to deprotection treatment), 3.27 mL of an aqueous 3N-sodium hydroxide solution was added thereto at room temperature, and the mixture was stirred overnight. The reaction mixture was diluted with water, and then, citric acid was added thereto until the solution became neutral. The precipitated crystals were collected by filtration, washed with water and dried under reduced pressure to obtain 2.015 g of N-tert-butoxycarbonyl-trans-4-[5-carboxy-2-(dimethylamino)pyrimidin-4-yloxy]cyclohexylamine.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-db71483c90064f3180f137312dc23f6d
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Reaction notes

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