Thiourea → 7beta-[alpha-ethoxyimino-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester

HRID 979680

反応式

HRID 979680 の反応式
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:43])[C@@H:24]([NH:25][C:26](=[O:42])[C:27]([C:32]3[N:33]=[C:34]([NH:37]C(=O)CCl)[S:35][CH:36]=3)=[N:28][O:29][CH2:30][CH3:31])[C@H:21]2[S:20][CH2:19][C:18]=1[CH:44]([S:46][C:47]1[NH:51][N:50]=[N:49][N:48]=1)[CH3:45])=[O:16])([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.NC(N)=S>O1CCCC1.C(O)C.[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:43])[C@@H:24]([NH:25][C:26](=[O:42])[C:27]([C:32]3[N:33]=[C:34]([NH2:37])[S:35][CH:36]=3)=[N:28][O:29][CH2:30][CH3:31])[C@H:21]2[S:20][CH2:19][C:18]=1[CH:44]([S:46][C:47]1[NH:51][N:50]=[N:49][N:48]=1)[CH3:45])=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 2723790ThioureaHCID 1784749067beta-{alpha-ethoxyimino-[2-(chloroacetamido)thiazol-4-yl]acetamido}-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester

生成物 1

HCID 1784749077beta-[alpha-ethoxyimino-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester収率 52.9%

試薬・触媒・溶媒 3

HCID 165294Benzyltriethylammonium bromide触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2.2 g of 7β-{α-ethoxyimino-[2-(chloroacetamido)thiazol-4-yl]acetamido}-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester in 20 ml of tetrahydrofuran is added a solution of 550 mg of thiourea in 20 ml of ethanol, followed by addition of 50 mg of triethylbenzylammonium bromide. The mixture is stired for 20 hours at room temperature and concentrated. The residue is dissolved in a mixture of ethyl acetate and tetrahydrofuran and the solution was washed with aq. sodium bicarbonate solution and then water, followed by drying over anhydrous magnesium sulfate. The dried solution is subjected to distillation of the solvent to give powder which is washed with chloroform and ether and dried. The procedure yields 1.047 g of 7β-[α-ethoxyimino-(2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester.

後処理

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in a mixture of ethyl acetate and tetrahydrofuran
  3. washthe solution was washed with aq. sodium bicarbonate solution
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe dried solution is subjected to distillation of the solvent
  6. customto give powder which
  7. washis washed with chloroform and ether
  8. customdried

出典と根拠

ORDレコード
ord-18149d32e1094153be181bbf82fb7180
出典データセット
uspto-grants-1987_05
特許番号
US04668783

関連ノート

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