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

HRID 1105612

反応式

HRID 1105612 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 additioal 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-242a03b6df324eef95b44a4343033111
出典データセット
uspto-grants-1982_01
特許番号
US04309442

関連ノート

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