Water → Trifluoroacetic acid

HRID 225960Notes

Reaction equation

HRID 225960 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][C@H:9]1[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=O)(C)(C)C.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].O>ClCCl>[OH:13][C@H:11]1[CH2:12][NH:8][C@H:9]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:10]1.[C:28]([OH:30])([C:27]([F:32])([F:31])[F:26])=[O:29]

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 69036723HCID 69036723, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 450832833-[(2R,4R)-4-Hydroxypyrrolidin-2-yl]propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((2R,4R)-1-(tert-butoxycarbonyl)-4-{[tert-butyl(dimethyl)silyl]oxy}-pyrrolidin-2-yl)propanoic acid (5.1 g, 13.65 mmol) in dichloromethane (100 ml) at 0° C. were added trifluoroacetic acid (14 ml) and water (3 ml). The reaction mixture was allowed to warm up and stirred overnight. The reaction mixture was concentrated in vacuo to afford 3-[(2R,4R)-4-hydroxypyrrolidin-2-yl]propanoic acid as TFA salt (3.74 g). Yield: 100%

Workup

  1. temperatureto warm up
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c483d8d8da79427eb8be6b1320f4c7b7
Source dataset
uspto-grants-2009_07
Patent number
US07557136B2

Reaction notes

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