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

HRID 1065674

반응식

HRID 1065674 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 14452Copper carbonate촉매HCID 23978Copper촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5eaf275ac0be40639d3d9b29563d9686
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04330559

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