HCID 69825528, compound → HCID 69825751, compound

HRID 1358091Notes

Reaction equation

HRID 1358091 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:13][C@@H:8]2[NH:9][C:10](=[O:12])[O:11][C@@H:7]2[C@H:6]1Br)=[O:4]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH2:13][C@@H:8]2[NH:9][C:10](=[O:12])[O:11][C@H:7]2[CH:6]=1)=[O:4]

Participants

3

Reactant 1

HCID 69825528HCID 69825528, compound

Product 1

HCID 69825751HCID 69825751, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DUB (75 ml, 0.5 mol) was added dropwise to a cooled solution (5° C.) of (3aS,5R,6S,6aS)-6-bromo-2-oxohexahydrocyclopentaoxazole-5-carboxylic acid methyl ester (110 g, 0.42 mol) in dichloromethane (400 ml). A mild exotherm was observed. After a further 15 mins reaction was complete. The reaction mixture was washed with 1 M HCl (aq) (2×150 ml), the aqueous washings back-extracted with dichlormethane (3×100 ml) and the combined organic extracts dried over magnesium sulfate. Following filtration, concentration of the organic solution gave the title compound as an off-white solid (75 g, 98%).

Workup

  1. customAfter a further 15 mins reaction
  2. washThe reaction mixture was washed with 1 M HCl (aq) (2×150 ml)
  3. extractionthe aqueous washings back-extracted with dichlormethane (3×100 ml)
  4. dry with materialthe combined organic extracts dried over magnesium sulfate
  5. filtrationfiltration, concentration of the organic solution

Sources & evidence

ORD record
ord-946eef69daa648acb86cb98a4a83fea6
Source dataset
uspto-grants-2003_07
Patent number
US06593489B1

Reaction notes

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