Benzyl chloroformate → HCID 13605332, compound

HRID 1284938Notes

Reaction equation

HRID 1284938 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1[S:16][CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])([O-:5])=[O:4].[CH2:23]([O:30][C:31](Cl)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[N+:3]([C:6]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:8][C:7]=1[S:16][CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH:19][C:31]([O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:32])([O-:5])=[O:4]

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 13605290HCID 13605290, compound

Product 1

HCID 13605332HCID 13605332, compound

Procedure

A mixture of 67 ml of 2.5N aqueous sodium hydroxide and 5.3 g of S-(2-nitro-4-trifluoromethylphenyl)-L-cysteine obtained in Reference Example 10 is stirred at room temperature for 30 minutes. Two point seven ml of benzyloxycarbonyl chloride and 19 ml of 1N aqueous sodium hydroxide are simultaneously added dropwise to the mixture at ice bath temperature over a period of 30 minutes. The resulting mixture is stirred at room temperature for further 2.5 hours and extracted with ethyl ether. The aqueous layer is acidified slightly with 1N hydrochloric acid and extracted with ethyl acetate. The extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is crystallized from ethyl ether to yield 5.5 g of S-(2-nitro-4-trifluoromethylphenyl)-N-benzyloxycarbonyl-L-cysteine as pale yellow crystals, m.p. 150°-153° C.

Workup

  1. customobtained in Reference Example 10
  2. stirringThe resulting mixture is stirred at room temperature for further 2.5 hours
  3. extractionextracted with ethyl ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is crystallized from ethyl ether

Sources & evidence

ORD record
ord-a81cd764d8554e79a097af6af2690e8a
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

Loading…