Hydrochloric Acid → 3-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

HRID 1155333노트

반응식

HRID 1155333 반응식
[BH4-].[Na+].[C:3]1([CH:9]([O:16][C:17]([C:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][C:20]=2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CN(C)C=O.C(O)(=O)C>[C:3]1([CH:9]([O:16][C:17]([C@@H:19]2[N:24]3[C:25](=[O:38])[C@@H:26]([NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:23]3[S:22][CH2:21][CH:20]2[OH:39])=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 547082513-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

생성물 1

HCID 705700963-Hydroxy-7beta-phenoxyacetylamino-cepham-4alpha-carboxylic acid diphenylmethyl ester

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

실험 절차

1.30 g of sodium borohydride are added in portions to a solution of 35.4 g of 3-hydroxy-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (crude product) in a mixture of 270 ml of dimethylformamide and 70 ml of glacial acetic acid in a stream of nitrogen while stirring and cooling with ice at approximately 15° to 20°. The reaction mixture is further stirred for one hour at room temperature, poured onto a mixture of ice and 2 N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed successively with 2 N hydrochloric acid, water, saturated, aqueous sodium bicarbonate solution and saturated, aqueous sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is substantially freed from dimethylformamide under a high vacuum and recrystallised from ethyl acetate and a little diethyl ether. The title compound is obtained which has a melting point of 167°-170°; Rf~0.47 (silica gel; toluene/ethyl acetate 1:1); [α]D20 =+88°± 1° (in chloroform, c=0.526%); IR spectrum (in CH2Cl2): Absorption bands up to 3580; 3410; 1780; 1740; 1695; 1600; 1518; 1494 cm-1.

후처리

  1. temperaturecooling with ice at approximately 15° to 20°
  2. stirringThe reaction mixture is further stirred for one hour at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed successively with 2 N hydrochloric acid, water
  5. dry with materialsaturated, aqueous sodium bicarbonate solution and saturated, aqueous sodium chloride solution, dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customrecrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-485b8042772c4f219c9c5ac0b2b29b55
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04301279

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