Hydroxyamine hydrochloride → HCID 131720180, compound

HRID 1376850Notes

Reaction equation

HRID 1376850 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:48][O:49][CH3:50])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([CH:46]=O)=[C:35]3[C:39]([O:41][C:42](C)(C)[CH3:43])=[O:40])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:52][OH:53]>N1C=CC=CC=1.CCOCC.C(OCC)(=O)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:48][O:49][CH3:50])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([CH:46]=[N:52][OH:53])=[C:35]3[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:28])[N:25]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 54289042HCID 54289042, compound

Product 1

HCID 131720180HCID 131720180, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an inert atmosphere, 142 mg of (1,1-dimethyl)ethyl 7-[2-(2-tritylamino-thiazol-4-yl)-2-methoxyimino-acetamido]-3-formyl-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate, (prepared in Step A of Example 52) and 42 mg of hydroxylamine hydrochloride were dissolved in 0.4 ml of pyridine and the solution was stirred for 50 minutes and diluted with ether and with ethyl acetate. The mixture was washed with 6 ml of N hydrochloric acid and after extracting the aqueous phase with ethyl acetate, the organic phases were dried and concentrated to dryness. The residue was chromatographed under pressure on silica and eluted with a mixture of ethyl acetate and methylene chloride (25-75) to obtain 91 mg of 1,1-dimethy]-ethyl 7-[2-(2-tritylamino-thiazol-4-yl)-2-methoxyimino-acetamido]-3-hydroxyiminomethyl-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate.

Workup

  1. washThe mixture was washed with 6 ml of N hydrochloric acid
  2. extractionafter extracting the aqueous phase with ethyl acetate
  3. customthe organic phases were dried
  4. concentrationconcentrated to dryness
  5. customThe residue was chromatographed under pressure on silica
  6. washeluted with a mixture of ethyl acetate and methylene chloride (25-75)

Sources & evidence

ORD record
ord-6657599228d447d492a9020ba8d802cf
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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