Hexachloroethane → (2S,4R)-4-tert-butoxy-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1527912Notes

Reaction equation

HRID 1527912 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[C:21](=[O:26])[NH:22][CH2:23][CH:24]=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:13][C@H:12]1[C:21]1[O:26][CH:24]=[CH:23][N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59548499(2S,4R)-4-tert-butoxy-2-(2-oxo-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 59548492(2S,4R)-4-tert-butoxy-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl esterYield 46.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (2S,4R)-4-tert-butoxy-2-(2-oxo-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (4.5 g, 12.43 mmol) and hexachloroethane (5.88 g, 24.86 mmol) in dichloromethane (30 mL) was added triphenyl phosphine (6.52 g, 24.86 mmol) The mixture was stirred at 0° C. for 15 min, triethylamine (2.5 g, 24.86 mmol) was then added and the mixture was stirred at room temp. for 14 h. The reaction mixture was then extracted with dichloromethane and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography (using 15% EtOAc in hexane as eluent) to give (2S,4R)-4-tert-butoxy-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester (2 g, 46.6% yield) as a yellow liquid. MS calcd. for C19H25N2O4 [(M+H)+] 345.0, obsd. 345.2.

Workup

  1. stirringthe mixture was stirred at room temp. for 14 h
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (using 15% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-0a1694a9d5c4432f8ad7a09c31456988
Source dataset
uspto-grants-2015_07
Patent number
US09090559B2

Reaction notes

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