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

HRID 977294

反応式

HRID 977294 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 14452Copper carbonate触媒HCID 23978Copper触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-51e12d4763664a24a9486d952de7c6c2
出典データセット
uspto-grants-1997_03
特許番号
US05614557

関連ノート

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