Bromotrichloromethane → (R)-methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)oxazole-4-carboxylate

HRID 2071110Notes

Reaction equation

HRID 2071110 reaction equation
COCCN(S(F)(F)F)CCOC.O[CH2:15][C@H:16]([NH:21][C:22]([C@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:23])[C:17]([O:19][CH3:20])=[O:18].BrC(Cl)(Cl)Cl.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH2:32]([O:31][C:29]([N:25]1[CH2:26][CH2:27][CH2:28][C@@H:24]1[C:22]1[O:23][CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[N:21]=1)=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 57506714HCID 57506714, compound

Product 1

HCID 66697570(R)-methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deoxo-flour (4.5 mL, 24.16 mmoles) was added drop-wise to a solution of (R)-benzyl 2-((S)-3-hydroxy-1-methoxy-1-oxopropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate (8.5 g, 22.0 mmoles) in CH2Cl2 (150 mL) at −20° C. The solution was stirred for 30 min and BrCCl3 (7.8 mL, 79.0 mmoles) was added drop-wise followed by DBU (11.8 mL, 79 mmoles). The reaction was stirred at 2-3° C., for 10 h., quenched with Satd. Aq. NaHCO3 solution and extracted with ethyl actetate. The organic layer was concentrated and chromatographed on silica gel (10% ethyl acetate/90% chloroform) to yield 6.95 of (R)-methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)oxazole-4-carboxylate.

Workup

  1. stirringThe reaction was stirred at 2-3° C., for 10 h.
  2. customquenched with Satd
  3. extractionAq. NaHCO3 solution and extracted with ethyl actetate
  4. concentrationThe organic layer was concentrated
  5. customchromatographed on silica gel (10% ethyl acetate/90% chloroform)

Sources & evidence

ORD record
ord-c3c0902606854b14a1f4a040d706cae1
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…