Water → HCID 59124112, compound

HRID 1392158Notes

Reaction equation

HRID 1392158 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C@@:7]23[CH2:14][C@H:13]([O:15]C(=O)C)[CH2:12][N:11]2[C:10](=[O:19])[N:9]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[C:8]3=[O:28])=[CH:4][CH:3]=1.O>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]23[CH2:14][C@H:13]([OH:15])[CH2:12][N:11]2[C:10](=[O:19])[N:9]([C:20]2[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=2)[C:8]3=[O:28])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 962WaterHCID 69212176HCID 69212176, compound

Product 1

HCID 59124112HCID 59124112, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5S,7S)-5-(4-bromobenzyl)-3-(3,5-dichloro-phenyl)-7-acetoxy-1,3-diazabicyclo[3.3.0]octane-2,4-dione (0.10 g) in THF (5 mL), MeOH (0.10 mL), and water (0.10 mL) was added 2N LIOH (0.11 mL). After 4 hours, the mixture was quenched with acetic acid (0.10 mL) and concentrated. Purification by chromatography (Silica gel: 4% methanol/CH2Cl2, Chromatotron) afforded the titled compound (0.0435 g). MS (m/z) 469 (MH+), mp 88.3° C.

Workup

  1. customthe mixture was quenched with acetic acid (0.10 mL)
  2. concentrationconcentrated
  3. customPurification by chromatography (Silica gel: 4% methanol/CH2Cl2, Chromatotron)

Sources & evidence

ORD record
ord-7200fe0c160d47a8bf6415acc82a931c
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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