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

HRID 1447637

Reaction equation

HRID 1447637 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-093901b511b341b28b69358266cc88b4
Source dataset
uspto-grants-1979_12
Patent number
US04177277

Linked notes

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