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 483032Notes

Reaction equation

HRID 483032 reaction equation
[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

Participants

9

Reactant 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

Product 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 acidYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-eb148e0e92a94896b948f4a144d767dc
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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