Trifluoroacetic acid → HCID 54587696, compound

HRID 1442950Notes

Reaction equation

HRID 1442950 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:22]([OH:24])=[O:23])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C@@H:11]2[CH2:12][NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59166756HCID 59166756, compound

Product 1

HCID 54587696HCID 54587696, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4S)-1-(tert-butoxycarbonyl)-4-[(4-chlorobenzyl)oxy]-2-pyrrolidinecarboxylic acid (Preparation 4, 96 mg, 0.38 mmol) was dissolved in dichloromethane (5 ml). Trifluoroacetic acid (5 ml) was added and the mixture left overnight at room temperature. The reaction mixture was partitioned between dichloromethane (25 ml) and water (25 ml). The aqueous layer was separated, washed with more dichloromethane (25 ml) and evaporated to dryness. The product was purified using Dowex™ 50WX8-200 resin, eluting first with water then 9:1 water:ammonia yielding the title compound (5 mg, 5% yield) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (25 ml) and water (25 ml)
  2. customThe aqueous layer was separated
  3. washwashed with more dichloromethane (25 ml)
  4. customevaporated to dryness
  5. customThe product was purified
  6. washeluting first with water

Sources & evidence

ORD record
ord-4ff56aa27d0e4da7961646b1a7c79078
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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