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

HRID 614795

Reaction equation

HRID 614795 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 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.

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-320052e21a354b5f866e314ca8896daa
Source dataset
uspto-grants-1979_03
Patent number
US04146611

Linked notes

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