Trifluoroacetic acid → (4S)-4-(Benzyloxy)-L-proline

HRID 1442951Notes

Reaction equation

HRID 1442951 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:21]([OH:23])=[O:22])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:14]([O:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:21]([OH:23])=[O:22])[CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140361811-(1,1-Dimethylethyl) (2S,4S)-4-(phenylmethoxy)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 15927507(4S)-4-(Benzyloxy)-L-prolineYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4S)-1-(tert-butoxycarbonyl)-4-(benzyloxy)-pyrrolidine-2-carboxylic acid (Preparation 17, 150 mg, 0.47 mmol) was dissolved in dichloromethane (5 ml). Trifluoroacetic acid (5 ml) was added and the mixture left stirring 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 an ion exchange column (Dowex 50WX8-200 resin), eluting first with water then 9:1 water:ammonia yielding the title compound (34 mg, 33% yield) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-6cbd0217bb5345f1bed11d9406e8cc7f
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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