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Acetic Acid → Benzhydryl 3-hydroxy-7-(phenylacetamido)cepham-4-carboxylate

HRID 1905795
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HRID 1905795 반응식
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[OH:36])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(O)(=O)C.O>CN(C)C=O>[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][CH:18]2[OH:36])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

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반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 54721268(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

생성물 1

HCID 13644573Benzhydryl 3-hydroxy-7-(phenylacetamido)cepham-4-carboxylate수율 76.3%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of 3-hydroxy-7beta-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (1) in dimethylformamide (9.5 parts, dried over Molecular Sieves) at -50° C. under nitrogen is added sodium borohydride (4 equivalents) at -53° to -48° C. over 3 minutes. After 30 minutes at the same temperature, glacial acetic acid (1.4 parts) and then water (10 parts) are added to the mixture gradually, and extracted with ethyl acetate. The extract is washed with 5% aqueous sodium hydrogen carbonate and water, dried over sodium sulfate, and concentrated. The residue is crystallized from a mixture of dichloromethane (4 parts) and n-hexane (1.7 parts) to give 3-hydroxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (2). Yield: 76.3%. mp. 196°-198° C. (decomposition).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with 5% aqueous sodium hydrogen carbonate and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is crystallized from a mixture of dichloromethane (4 parts) and n-hexane (1.7 parts)

출처 및 근거

ORD 기록
ord-1ecf83c774844dd3b05b38f156ea281f
출처 데이터셋
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04647658

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