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

HRID 483040Notes

Reaction equation

HRID 483040 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])/[C:27]([OH:29])=O)[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.[NH2:65][C@@H:66]1[C:84](=[O:85])[N:68]2[C:69]([C:81]([OH:83])=[O:82])=[C:70]([CH2:73][S:74][C:75]3[N:79]([NH2:80])[N:78]=[N:77][N:76]=3)[CH2:71][S:72][C@H:67]12.C(N(CC)CC)C.NC1C(CSC2N(NC(C)C)N=NN=2)=C(C(O)=O)N2C(=O)C[C@H]2S1>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][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])/[C:27]([NH:65][C@@H:66]2[C:84](=[O:85])[N:68]3[C:69]([C:81]([OH:83])=[O:82])=[C:70]([CH2:73][S:74][C:75]4[N:79]([NH2:80])[N:78]=[N:77][N:76]=4)[CH2:71][S:72][C@H:67]23)=[O:29])[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

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13078701(2Z)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acidHCID 133675107beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 131714570Amino-3-[(1-isopropylamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 141545485(6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tert-butoxycarbonylmethoxyimino)acetic acid (3.80 g, 7 mmol), 1-hydroxybenzotriazole (1.09 g, 8.05 mmol) and N,N'-dicyclohexylcarbodiimide (1.59 g, 7.7 mmol) in dimethylacetamide (40 ml) was stirred at room temperature for 2 hours. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.76 g, 8.4 mmol) and triethylamine (1.70 g, 16.8 mmol) in dimethylacetamide (20 ml) and water (2.8 ml) and the mixture was stirred 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 brown powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tert-butoxycarbonylmethoxyimino)acetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (4.96 g, 83%).

Workup

  1. additionThen the mixture was treated in a manner similar to

Sources & evidence

ORD record
ord-b45f2eddde7844199a0384f3f9ed9b3e
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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