Triethylamine → (6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-[2-(methylamino)-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 483038Notes

Reaction equation

HRID 483038 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:36])[NH:34][CH3:35])/[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.[NH2:62][C@@H:63]1[C:81](=[O:82])[N:65]2[C:66]([C:78]([OH:80])=[O:79])=[C:67]([CH2:70][S:71][C:72]3[N:76]([NH2:77])[N:75]=[N:74][N:73]=3)[CH2:68][S:69][C@H:64]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:36])[NH:34][CH3:35])/[C:27]([NH:62][C@@H:63]2[C:81](=[O:82])[N:65]3[C:66]([C:78]([OH:80])=[O:79])=[C:67]([CH2:70][S:71][C:72]4[N:76]([NH2:77])[N:75]=[N:74][N:73]=4)[CH2:68][S:69][C@H:64]23)=[O:28])[N:25]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 133675107beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 88485603(2Z)-2-[2-(methylamino)-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acidHCID 131714570Amino-3-[(1-isopropylamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 13262016(6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-[2-(methylamino)-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 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(N-methylcarbamoyl)methoxyiminoacetic acid (3.25 g, 6.5 mmol), 1-hydroxybenzotriazole (0.97 g, 7.15 mmol) and N,N'-dicyclohexylcarbodiimide (1.41 g, 6.83 mmol) in dimethylacetamide (34 ml) was stirred at room temperature for 4 hours. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.57 g, 7.8 mmol) and triethylamine (1.73 g, 17.2 mmol) in dimethylacetamide (20 ml) and water (2.4 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-(N-methylcarbamoyl)methoxyiminoacetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (4.1 g, 78%).

Workup

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

Sources & evidence

ORD record
ord-b9046257e0fd4c69b883d791364ae2a6
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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