Triethylamine → (6R,7R)-7-[[(2Z)-2-(1-amino-2-methyl-1-oxopropan-2-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 483032노트

반응식

HRID 483032 반응식
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:35](=[O:37])[NH2:36])([CH3:34])[CH3:33])/[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([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.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:63][C@@H:64]1[C:82](=[O:83])[N:66]2[C:67]([C:79]([OH:81])=[O:80])=[C:68]([CH2:71][S:72][C:73]3[N:77]([NH2:78])[N:76]=[N:75][N:74]=3)[CH2:69][S:70][C@H:65]12.C(N(CC)CC)C.NC1SC=C(/C(=N/OCCCC)/C(N[C@@H]2C(=O)N3C(C(O)=O)=C(CSC4N(N)N=NN=4)CS[C@H]23)=O)N=1>CC(N(C)C)=O.O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C:32]([C:35](=[O:37])[NH2:36])([CH3:34])[CH3:33])/[C:27]([NH:63][C@@H:64]2[C:82](=[O:83])[N:66]3[C:67]([C:79]([OH:81])=[O:80])=[C:68]([CH2:71][S:72][C:73]4[N:77]([NH2:78])[N:76]=[N:75][N:74]=4)[CH2:69][S:70][C@H:65]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

9

반응물 6

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 133675107beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 88675921(2Z)-2-(1-amino-2-methyl-1-oxopropan-2-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acidHCID 178454536(6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-butoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

생성물 1

HCID 13262002(6R,7R)-7-[[(2Z)-2-(1-amino-2-methyl-1-oxopropan-2-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid수율 70.5%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매2회

실험 절차

A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-carbamoyl-2-propyloxyimino)acetic acid (2.00 g, 3.9 mmol), 1-hydroxybenzotriazole (0.560 g, 4.29 mmol) and N,N'-dicyclohexylcarbodiimide (0.840 g, 4.10 mmol) in dimethylacetamide (24 ml) was stirred at room temperature for 4 hours. To this solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (1.41 g, 4.29 mmol) and triethylamine (0.790 g, 8.58 mmol) in dimethylacetamide (10 ml) and water (1.4 ml) and the mixture was allowed to react at room temperature for 17 hours. Then the mixture was treated in a manner similar to that described in Example 6, (c) to give pale yellow powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-carbamoyl-2-propyloxyimino)acetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.27 g, 70.5%).

후처리

  1. customto react at room temperature for 17 hours
  2. additionThen the mixture was treated in a manner similar to

출처 및 근거

ORD 기록
ord-eb148e0e92a94896b948f4a144d767dc
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04576938

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