Citric Acid → HCID 68530977, compound

HRID 644195Notes

Reaction equation

HRID 644195 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl-].[Na+].O.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68532527HCID 68532527, compound

Product 1

HCID 68530977HCID 68530977, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of methyl 2-(2-tert-butoxycarbonylaminoethoxy)-4-fluorobenzoate (4.2 g, 13.4 mmol), THF (100 mL), and MeOH (50 mL) was treated with 1 M lithium hydroxide (16 mL) and stirred for 48 hours at ambient temperature. The reaction was acidified with 10% aqueous citric acid (50 mL), diluted with brine (100 mL), and extracted with EtOAc (3×100 mL). The combined organic layers were dried over MgSO4 and concentrated to give 3.93 g (13.1 mmol, 98%) of a white solid.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f48f73ee29a5484e815e321f08426650
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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