Triethylamine → 2,2,2-trichloroethyl 2-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylate

HRID 1764006ノート

反応式

HRID 1764006 の反応式
[CH:1]1([CH:4]([O:6][C:7]([N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][C:11]([OH:13])=O)=[O:8])[CH3:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC)=O.Cl.[CH3:34][CH:35]1[CH:40]=[C:39]([C:41]([O:43][CH2:44][C:45]([Cl:48])([Cl:47])[Cl:46])=[O:42])[N:38]2[C:49](=[O:52])[CH:50]([NH2:51])[C@H:37]2[S:36]1>CN(C)CC1C=CC=CC=1.ClCCl>[CH3:34][CH:35]1[CH:40]=[C:39]([C:41]([O:43][CH2:44][C:45]([Cl:48])([Cl:46])[Cl:47])=[O:42])[N:38]2[C:49](=[O:52])[CH:50]([NH:51][C:11](=[O:13])[CH2:10][N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]([O:6][CH:4]([CH:1]3[CH2:2][CH2:3]3)[CH3:5])=[O:8])[C@H:37]2[S:36]1

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 10928Ethyl chloroformateHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochlorideHCID 53938438N-(1-cyclopropylethoxycarbonyl)phenylglycine

生成物 1

HCID 1317112512,2,2-trichloroethyl 2-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylate収率 88.2%

試薬・触媒・溶媒 2

HCID 7681N,N-Dimethylbenzylamine触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of N-(1-cyclopropylethoxycarbonyl)phenylglycine (1.63 g), triethylamine (0.60 g) and dimethylbenzylamine (2 drops) in dried dichloromethane (10 ml) was dropwise added at -10° C. to a solution of ethyl chloroformate (0.67 g) in dried dichloromethane (15 ml), and the mixture was stirred for 1 hour. The mixture was cooled at -10° to 15° C. and to the mixture was dropwise added over 10 minutes a solution of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (2.2 g) and triethylamine (0.55 g) in dried dichloromethane (20 ml), after which the mixture was stirred for 2.5 hours at the same temperature. After the reaction, the reaction mixture was in turn washed with water, 2% hydrochloric acid, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was pulverized by adding isopropyl ether, after which the powder was collected by filtration and dried to give 2,2,2-trichloroethyl 2-methyl-7-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]amino-3-cephem-4-carboxylate (3.0 g), mp 165° to 167.5° C.

後処理

  1. temperatureThe mixture was cooled at -10° to 15° C. and to the mixture
  2. stirringafter which the mixture was stirred for 2.5 hours at the same temperature
  3. customAfter the reaction
  4. washwashed with water, 2% hydrochloric acid
  5. dry with materiala saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. additionby adding isopropyl ether
  8. filtrationafter which the powder was collected by filtration
  9. customdried

出典と根拠

ORDレコード
ord-36e78ecbc5ef4884add61457a7bdb2a3
出典データセット
uspto-grants-1978_09
特許番号
US04113940

反応ノート

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