Sodium Hydroxide → 1-[2-Acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline

HRID 1447637

반응식

HRID 1447637 반응식
[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH2:11][CH2:12][NH2:13])[C:7]([OH:9])=O)(=[O:3])[CH3:2].C1C([N+]([O-])=O)=CC=C(O[C:24]([C:26]([F:29])([F:28])[F:27])=[O:25])C=1.[NH:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=[O:33].[OH-].[Na+]>N1C=CC=CC=1.O>[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH2:11][CH2:12][NH:13][C:24](=[O:25])[C:26]([F:27])([F:28])[F:29])[C:7]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=[O:33])=[O:9])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 695694-Nitrophenyl trifluoroacetateHCID 145742L-ProlineHCID 134246592-[(Acetylsulfanyl)methyl]-5-aminopentanoic acid

생성물 1

HCID 540982051-[2-Acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

A mixture of 2-acetylthiomethyl-5-aminopentanoic acid (2.05 g.) and p-nitrophenyltrifluoroacetate (5.6 g.) in pyridine (10 ml.) is stirred at room temperature for four hours, and then added dropwise to a vigorously stirred solution of L-proline (1.55 g.) in water (10 ml.) while keeping the pH at 9 with careful addition of 2 N sodium hydroxide. When the consumption of sodium hydroxide stops, the reaction mixture is acidified with hydrochloric acid and extracted with ethyl acetate. The solvent is removed in vacuo and the residue is chromatographed on a silica gel column to yield 1-[2-acetylthiomethyl-5-(trifluoroacetylamino)pentanoyl]-L-proline.

후처리

  1. customWhen the consumption of sodium hydroxide
  2. extractionextracted with ethyl acetate
  3. customThe solvent is removed in vacuo
  4. customthe residue is chromatographed on a silica gel column

출처 및 근거

ORD 기록
ord-093901b511b341b28b69358266cc88b4
출처 데이터셋
uspto-grants-1979_12
특허 번호
US04177277

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