Water → HCID 57219190, compound

HRID 1591272Notes

Reaction equation

HRID 1591272 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH2:16][CH2:17][C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[NH:14][C:13]1=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].O>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH2:16][CH2:17][C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[N:14]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:13]1=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 79177tert-Butyl bromoacetate2×HCID 57179522HCID 57179522, compound

Product 1

HCID 57219190HCID 57219190, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Triton B (1.94 mL, 4.3 mmols) was added dropwise to a stirred, cooled (-30° C.) solution of (3S,4R)-3-benzyloxycarbonylamino-4-[2-(2-furyl)ethyl]azetidin-2-one (1.35 g, 4.3 mmols) in N,N-dimethylformamide (15 mL). Stirring was continued for 0.25 hr. at -30° C. The mixture was allowed to warm to 0° C. during about 0.25 hr and then was recooled to -30° C. when a solution of t-butyl bromoacetate (0.764 mL, 4.73 mmols) in DMF (3 mL) was added dropwise. Stirring was continued at -30° C. for 0.25 hr., 1 hr at 0° C. and then for 2 hr at ambient temperatures, when additional t-butyl bromoacetate (0.3 mL) was added. The mixture was stirred for an additional 1 hr and was poured into H2O. The mixture was extracted twice with ethyl acetate. The extracts were washed twice with H2O, followed by saturated NaCl and then dried over MgSO4. The ethyl acetate was removed and the residue flash chromatographed on SiO2 (40 g) with methylene chloride - methanol (98:2) to afford 1.47 g (80% yield) of the title compound as a viscous oil which crystallized. Recrystallization from ethyl acetate-hexanes afforded colorless crystals, mp 82°-84° C.

Workup

  1. additionTriton B (1.94 mL, 4.3 mmols) was added dropwise to a stirred
  2. customat -30° C
  3. customwas recooled to -30° C.
  4. additionwas added dropwise
  5. stirringStirring
  6. waitwas continued at -30° C. for 0.25 hr
  7. stirringThe mixture was stirred for an additional 1 hr
  8. extractionThe mixture was extracted twice with ethyl acetate
  9. washThe extracts were washed twice with H2O
  10. dry with materialdried over MgSO4
  11. customThe ethyl acetate was removed
  12. customthe residue flash chromatographed on SiO2 (40 g) with methylene chloride - methanol (98:2)

Sources & evidence

ORD record
ord-907bb69876794308a8ef4424c179f85f
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

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