Benzyl chloroformate → HCID 14650087, compound

HRID 1722742Notes

Reaction equation

HRID 1722742 reaction equation
[NH2:1][CH:2]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[OH-].[Na+].CCOCC>[CH2:11]([O:18][C:19]([NH:1][CH:2]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)[C:3]([OH:5])=[O:4])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 1025772-Amino-2-(thiophen-3-yl)acetic acid

Product 1

HCID 14650087HCID 14650087, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

2-Amino-2-(3-thienyl)acetic acid (10 g) is dissolved in 1N sodium hydroxide solution, and 1N sodium hydroxide solution and a solution of benzyloxycarbonyl chloride (13 g) in ether are simultaneously added dropwise thereto at 5° to 10° C. with vigorous stirring. The mixture is stirred at the same temperature for 3 hours. After the reaction mixture is washed, the mixture is acidified and extracted with ethyl acetate. The extract is washed, dried and concentrated to remove solvent. The residue is crystallized with a mixture of ethyl acetate and diisopropyl ether, whereby 2-benzyloxycarbonylamino-2-(3-thienyl)acetic acid (13.6 g) is obtained.

Workup

  1. customat 5° to 10° C.
  2. washAfter the reaction mixture is washed
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed
  5. customdried
  6. concentrationconcentrated
  7. customto remove solvent
  8. customThe residue is crystallized with a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-830696b1666e4a5684de8f66f60d01c2
Source dataset
uspto-grants-1989_08
Patent number
US04857543

Reaction notes

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