Dichloromethane → HCID 23388198, compound

HRID 1839346Notes

Reaction equation

HRID 1839346 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.ClCCl>C1C=CC=CC=1.[Cl-].[Na+].O.O[C@@H]([C@H]1C(=O)N2C(C(OCOC(=O)C(C)(C)C)=O)=C(C3SC4=C(C(=O)CC)N=CN4C=3)[C@H](C)[C@H]12)C>[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 3

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

Product 1

HCID 23388198HCID 23388198, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 23388045HCID 23388045, compoundCatalystHCID 241BenzeneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4Nitrobenzyl (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-e3902f8ca3d14111a669b49a5e55e6ca
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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