Ammonium Chloride → HCID 70634358, compound

HRID 1283721Notes

Reaction equation

HRID 1283721 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH:21][C:22](=[O:30])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:19](=[O:31])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:3])[CH3:2].C[O-].[Li+].Cl[O:36][C:37](C)(C)C.[Cl-].[NH4+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CO.O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@:20]([O:36][CH3:37])([NH:21][C:22](=[O:30])[CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:19](=[O:31])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])(=[O:3])[CH3:2]

Participants

10

Reactant 5

HCID 25517Ammonium ChlorideHCID 521297Tert-Butyl hypochloriteHCID 656671Sodium PyrosulfiteHCID 4177230Lithium methanolateHCID 44825458HCID 44825458, compound

Product 1

HCID 70634358HCID 70634358, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A cooled (-78°) solution of t-butyl (6R,7R)-3-acetoxymethyl-7-phenylacetamidoceph-3em-4-carboxylate (1.5 g.) in dry tetrahydrofuran (10 ml) was added over 3 minutes to a stirred and cooled (-78°) solution of lithium methoxide (358 mg) in dry methanol (8.8 ml) and tetrahydrofuran (50 ml) under nitrogen. t-Butyl hypochlorite (0.69 ml) was added after 3 minutes, and sitrring was continued for a further 5 minutes when the yellow solution was poured into a stirred mixture of ethyl acetate (150 ml) and water (150 ml) containing ammonium chloride (1 g) and sodium metabisulphite (1 g.). The aqueous phase was separated and extracted with ethyl acetate (50 ml) and the organic phases were combined and washed with brine (50 ml) and dried and evaporated to dryness in vacuo to give t-butyl (6R,7S)-3-acetoxymethyl-7-methoxy-7-phenylacetamidoceph-3-em-4-carboxylate (1.6 g).

Workup

  1. additionwas added over 3 minutes to
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate (50 ml)
  4. washwashed with brine (50 ml)
  5. customdried
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-c2a4eeb92c9d4d4f8f54d1b3e5008e5c
Source dataset
uspto-grants-1976_08
Patent number
US03976546

Reaction notes

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