Dichloromethane → HCID 23388198, compound

HRID 989883Notes

Reaction equation

HRID 989883 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:34](=[O:35])[N:6]2[C:7]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH3:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Br:36]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.ClCCl>C1C=CC=CC=1.[Cl-].[Na+].O>[Br:36][C:18]1[N:13]2[C:14]([S:15][C:11]([C:8]3[C@H:9]([CH3:10])[C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:34](=[O:35])[N:6]4[C:7]=3[C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:22])=[CH:12]2)=[C:16]([S:19][CH3:20])[N:17]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 23388233HCID 23388233, compound

Product 1

HCID 23388198HCID 23388198, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Nitrobenzyl(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo-[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (77 mg) was dissolved in 5 ml of benzene at room temperature. N-bromosuccinimide (33 mg) and 5 mg of 2,2′-azobis(isobutyronitrile) were added to the solution. The mixture was stirred for 10 min. Dichloromethane (10 ml) and 10 ml of semisaturated brine were added thereto, followed by separation. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to give 70 mg of 4-nitrobenzyl(1S,5R,6S)-2-(5-bromo-7-methylthioimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. customfollowed by separation
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-5731c3d2694c4aee9a185322bcda0772
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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