Bromotrichloromethane → (R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylate

HRID 2070995Notes

Reaction equation

HRID 2070995 reaction equation
COCCN(S(F)(F)F)CCOC.[C:14]([O:18][C:19]([NH:21][C@H:22]([CH3:33])[C:23]([NH:25][CH:26]([CH2:31][OH:32])[C:27]([O:29][CH3:30])=[O:28])=O)=[O:20])([CH3:17])([CH3:16])[CH3:15].BrC(Cl)(Cl)Cl>C(Cl)Cl>[C:14]([O:18][C:19]([NH:21][C@@H:22]([C:23]1[O:32][CH:31]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[N:25]=1)[CH3:33])=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 57486672methyl 2-((R)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxypropanoate

Product 1

HCID 68671221(R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deoxo-fluor™ (Bis-(2-methoxy)amino sulfur trifluoride, 1.4 mL, 7.6 mmol) was added drop-wise to a solution of methyl 2-((R)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxypropanoate (2.0 g, 6.9 mmol) in CH2Cl2 (50 mL) at −20° C. The solution was stirred for 30 min and BrCCl3 (2.45 mL, 24.8 mmol) was added drop-wise. The reaction was stirred at 2-3° C., for 8 h., quenched with sat. aq. NaHCO3 solution and extracted with ethyl acetate. The organic layer was concentrated and chromatographed on silica gel (30% ethyl acetate/70% hexanes) to yield 65% of (R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylate.

Workup

  1. stirringThe reaction was stirred at 2-3° C., for 8 h.
  2. customquenched with sat. aq. NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customchromatographed on silica gel (30% ethyl acetate/70% hexanes)

Sources & evidence

ORD record
ord-1e0ca2a36f8e4d0f96264870200284d5
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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