Dimethylformamide → HCID 178451131, 화합물

HRID 895068

반응식

HRID 895068 반응식
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH:9]([S:14][C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH2:10][C:11]([OH:13])=[O:12])[CH2:7][S:8][C@H:3]12.CN(C)C=O.C(N(CC)CC)C.[C:37]([O:41][C:42]([CH:44]([C:48]1[S:49][CH:50]=[CH:51][CH:52]=1)[C:45](N)=[O:46])=[O:43])([CH3:40])([CH3:39])[CH3:38]>C(N)=O.CCOCC>[C:37]([O:41][C:42]([CH:44]([C:48]1[S:49][CH:50]=[CH:51][CH:52]=1)[C:45]([NH:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH:9]([S:14][C:15]3[NH:16][N:17]=[N:18][N:19]=3)[CH2:10][C:11]([OH:13])=[O:12])[CH2:7][S:8][C@H:3]12)=[O:46])=[O:43])([CH3:40])([CH3:38])[CH3:39]

참가 물질

7

반응물 4

HCID 6228Dimethylformamide2회HCID 8471TriethylamineHCID 21315147alpha-t-ButoxycarbonylthienylacetamideHCID 178508097HCID 178508097, 화합물

생성물 1

HCID 178451131HCID 178451131, 화합물

시약·촉매·용매 2

HCID 713Formamide촉매HCID 3283Diethyl Ether용매

실험 절차

7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (1.0 g., 2.68 mmol.) was suspended in 10 ml. of dry dimethylformamide and 1.12 ml. of triethylamine was added followed by 85 drops of formamide. A solution of 0.91 g. (2.68 mmol.) of the activated ester of α-t-butoxycarbonylthienylacetamide, prepared as described above, in 2 ml. of dimethylformamide was added and the reaction mixture was stirred at 25° for three hours. An additional 0.45 g. of activated ester was then added and the mixture stirred another five hours. Ether (ca. 300 ml.) was added and the solution was decanted. The remaining oily material was washed with ether, dissolved in water and the aqueous solution was extracted with ethyl acetate. The pH of the ethyl acetate solution was adjusted to 1.5 by addition of dilute hydrochloric acid. Extraction with ethyl acetate and evaporation of the solvent gave 7-(α-t-butoxycarbonylthienylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid.

후처리

  1. stirringthe mixture stirred another five hours
  2. customthe solution was decanted
  3. washThe remaining oily material was washed with ether
  4. dissolutiondissolved in water
  5. extractionthe aqueous solution was extracted with ethyl acetate
  6. additionThe pH of the ethyl acetate solution was adjusted to 1.5 by addition of dilute hydrochloric acid
  7. extractionExtraction
  8. customwith ethyl acetate and evaporation of the solvent

출처 및 근거

ORD 기록
ord-3c0bb7e1f7bf4e45b896cdd0ceaf9a1b
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04286089

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