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Hydrogen Sulfide → 2-Amino-5-benzyloxycarbonylamino-2-difluoromethylpentanoic acid

HRID 977294
Notes
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Reaction equation

HRID 977294 reaction equation
[F:1][CH:2]([F:12])[C:3]([NH2:11])([CH2:7][CH2:8][CH2:9][NH2:10])[C:4]([OH:6])=[O:5].Cl.O.FC(F)C(N)(CCCN)C(O)=O.[CH2:27]([O:34][C:35](Cl)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.S>O.[Cu].C(=O)([O-])[O-].[Cu+2]>[NH2:11][C:3]([CH:2]([F:12])[F:1])([CH2:7][CH2:8][CH2:9][NH:10][C:35]([O:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:36])[C:4]([OH:6])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 402Hydrogen SulfideHCID 3009EflornithineHCID 10387Benzyl chloroformateHCID 441361Ornithine, 2-(difluoromethyl)-, hydrochloride, hydrate (1:1:1)

Product 1

HCID 112207982-Amino-5-benzyloxycarbonylamino-2-difluoromethylpentanoic acid

Reagents, catalysts & solvents 3

HCID 14452
Copper carbonate
Catalyst
HCID 23978CopperCatalyst
HCID 962WaterSolvent

Procedure

To a solution of the copper salt of 2-difluoromethyl-2,5-diaminopentanoic acid in water, prepared by reacting 2-difluoromethyl-2,5-diaminopentanoic acid monohydrate hydrochloride (2.4 g) with copper carbonate (6 g), is added slowly at 0° C. with stirring 1.1 g of benzylchloroformate. The reaction mixture is stirred for an additional 3 hours at room temperature after which hydrogen sulfide is passed through the solution until it becomes colorless. The precipitate is filtered off, and the pH of the aqueous solution is adjusted to 6 by the addition of hydrochloric acid. Upon concentration 2-amino-5-benzyloxycarbonylamino-2-difluoromethylpentanoic acid is obtained.

Workup

  1. additionis added slowly at 0° C.
  2. filtrationThe precipitate is filtered off
  3. additionthe pH of the aqueous solution is adjusted to 6 by the addition of hydrochloric acid
  4. concentrationUpon concentration 2-amino-5-benzyloxycarbonylamino-2-difluoromethylpentanoic acid
  5. customis obtained

Sources & evidence

ORD record
ord-51e12d4763664a24a9486d952de7c6c2
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05614557

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes