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Water → diphenylmethyl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1071312
Notes
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Reaction equation

HRID 1071312 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:19]([O:21][CH:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])=[C:15]([OH:18])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48].O>C(#N)C>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:19]([O:21][CH:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:20])=[C:15]([O:18][S:47]([CH3:46])(=[O:49])=[O:48])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54721268(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Product 1

HCID 11050121diphenylmethyl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Yield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-40 °C

Procedure

Benzhydryl 7β-[(phenylacetyl)amino]-3-hydroxy-3-cephem-4-carboxylate (500 g, 1 mol) was dissolved in acetonitrile (2 L) and ethyldiisopropylamine (183 mL, 1.05 mol) was added dropwise over 10 min with stirring at −40° C. Then, methanesulfonyl chloride (86 mL, 1.1 mol) was added dropwise over 10 min and the mixture was stirred at −40° C. for 40 min. The reaction mixture was poured into iced water (8 L) and the precipitate was collected by filtration. The precipitate was washed with water (2 L) and ethyl acetate (300 mL) and dried under reduced pressure to give the title compound (544 g, 0.94 mol) as pale-yellow crystals. yield: 94%.

Workup

  1. stirringthe mixture was stirred at −40° C. for 40 min
  2. filtrationthe precipitate was collected by filtration
  3. washThe precipitate was washed with water (2 L) and ethyl acetate (300 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-8d246489607c43d4992487aecaebf320
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06906055B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes