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Sodium Carbonate → (2R,4S)-4-Hydroxy-1-[4-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl ester

HRID 455274
Notes
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Reaction equation

HRID 455274 reaction equation
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][NH:7]1)=[O:5].C([O-])([O-])=O.[Na+].[Na+].[N:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:23][CH:22]=1)=[C:19]=[O:20]>C1COCC1>[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][N:7]1[C:19](=[O:20])[NH:18][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([F:31])([F:30])[F:32])=[CH:23][CH:22]=1)=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 44118802Methyl (2R,4S)-4-hydroxypyrrolidine-2-carboxylate hydrochlorideHCID 539725321-Isocyanato-4-(2,2,2-trifluoro-ethoxy)-benzene

Product 1

HCID 70976230(2R,4S)-4-Hydroxy-1-[4-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a solution of (2R,4S)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester, hydrochloride (3 g, 16.57 mmol) in THF (15 mL) was added solid Na2CO3 (2.10 g, 19.88 mmol) and stirred for 15 min. To this mixture, freshly prepared 1-Isocyanato-4-(2,2,2-trifluoro-ethoxy)-benzene (4.3 g, 19.88 mmol) in THF (10 mL) was added and stirred for 2 h at room temperature. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was taken up in DCM and washed with water and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography over silica (5% MeOH in DCM) to yield 2.7 g (50%) of the title compound as a white solid. LC-MS: 363.2 [M+1]+.

Workup

  1. stirringstirred for 2 h at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography over silica (5% MeOH in DCM)

Sources & evidence

ORD record
ord-93e972e0e1d24e799fb2da8e0852dafb
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497288B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes