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

HRID 614795

反応式

HRID 614795 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

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 2N 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.

後処理

  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

出典と根拠

ORDレコード
ord-320052e21a354b5f866e314ca8896daa
出典データセット
uspto-grants-1979_03
特許番号
US04146611

関連ノート

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