Triethylamine → HCID 178514051, compound

HRID 483033Notes

Reaction equation

HRID 483033 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])[NH2:34])/[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.[NH2:61][C@@H:62]1[C:80](=[O:81])[N:64]2[C:65]([C:77]([OH:79])=[O:78])=[C:66]([CH2:69][S:70][C:71]3[N:75]([NH2:76])[N:74]=[N:73][N:72]=3)[CH2:67][S:68][C@H:63]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][CH2:32][C:33](=[O:35])[NH2:34])/[C:27]([NH:61][C@@H:62]2[C:80](=[O:81])[N:64]3[C:65]([C:77]([OH:79])=[O:78])=[C:66]([CH2:69][S:70][C:71]4[N:75]([NH2:76])[N:74]=[N:73][N:72]=4)[CH2:67][S:68][C@H:63]23)=[O:29])[N:25]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 12816813(2Z)-2-(2-amino-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 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 178514051HCID 178514051, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-carbamoylmethoxyiminoacetic acid (3.02 g, 6.2 mmol), 1-hydroxybenzotriazole (0.900 g, 6.7 mmol) and N,N'-dicyclohexylcarbodiimide (1.38 g, 6.7 mmol) in dimethylacetamide (17 ml) was stirred at 0°-5° C. for an hour. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.38 g, 7.2 mmol) and triethylamine (1.60 g, 15.8 mmol) in dimethylacetamide (12 ml) and water (2 ml) at the same temperature and allowed to react for 2 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-carbamoylmethoxyiminoacetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (3.43 g, 69.3%), mp~115° C. (decomposition).

Workup

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

Sources & evidence

ORD record
ord-2c4d00ff31164fffb2b8ec94f31ce57d
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

Loading…