1,2-Dimethoxyethane → 7beta-Phenylacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

HRID 1155450

반응식

HRID 1155450 반응식
[C:1]1([CH:7]([O:14][C:15](=[O:47])/[C:16](/[N:21]2[CH:24]([S:25]S(C3C=CC(C)=CC=3)(=O)=O)[CH:23]([NH:36][C:37](=[O:45])[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:22]2=[O:46])=[C:17](\[O:19][CH3:20])/[CH3:18])[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.COCCOC.N12CCCCC1C=NCCC2>C1(C)C=CC=CC=1>[C:8]1([CH:7]([O:14][C:15]([C@@H:16]2[N:21]3[C:22](=[O:46])[C@@H:23]([NH:36][C:37](=[O:45])[CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@H:24]3[S:25][CH:18]=[C:17]2[O:19][CH3:20])=[O:47])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 80711,2-DimethoxyethaneHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 705571822-[4-(p-Toluenesulphonylthio)-3-phenylacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester

생성물 1

HCID 704484817beta-Phenylacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid diphenylmethyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 670 mg (1 mmol) of 2-[4-(p-toluenesulphonylthio)-3-phenylacetamido-2-oxoazetidin-1-yl]-3-methoxycrotonic acid diphenylmethyl ester, 6.7 ml of 1,2-dimethoxyethane and 0.22 ml of 1,5-diazabicyclo[5.4.0]undec-5-ene is stirred for 25 minutes at room temperature under a nitrogen atmosphere. The reaction mixture is diluted with toluene, washed successively with 2 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated by evaporation in vacuo. The residue, after preparative thick layer chromatography on silica gel using toluene/ethyl acetate, 1:1, gives 7β-phenylacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid diphenylmethyl ester of melting point 166°-169° C. (from methylene chloride/hexane), UV spectrum (ethanol): λmax =258 mμ (ε=4,500), IR spectrum (methylene chloride) characteristic bands at 2.93, 5.62, 5.73, 5.93 and 6.66μ, Rf value~0.54 (silica gel; system toluene/ethyl acetate, 1:1), and amorphous 7β-phenylacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester, UV spectrum (ethanol): λmax =258 mμ (ε=6,350), 264 mμ (β=6,350), 282 mμ (ε=5,600) (shoulder), IR spectrum (methylene chloride): characteristic bands at 2.94, 5.63, 5.83, 5.94, 6.26 and 6.66μ, Rf value~0.37 (silica gel; system toluene/ethyl acetate, 1:1), in the ratio of 8:1.

후처리

  1. washwashed successively with 2 N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation in vacuo

출처 및 근거

ORD 기록
ord-38b9590af16a403494ee15382b5c6d0b
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04301278

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