Water → (6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-butoxyimino-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 483031Notes

Reaction equation

HRID 483031 reaction equation
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]([NH2:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[C:29]([NH:48][C:49]1[S:50][CH:51]=[C:52](/[C:54](=[N:67]/[O:68][CH2:69][CH2:70][CH2:71][CH3:72])/[C:55](ON2C3C=CC=CC=3N=N2)=[O:56])[N:53]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O.C(NC1SC=C(/C(=N/OC)/C(N[C@@H]2C(=O)N3C(C(O)=O)=C(CSC4N(NC(=O)C)N=NN=4)CS[C@H]23)=O)N=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CC(N(C)C)=O>[C:29]([NH:48][C:49]1[S:50][CH:51]=[C:52](/[C:54](=[N:67]/[O:68][CH2:69][CH2:70][CH2:71][CH3:72])/[C:55]([NH:1][C@@H:2]2[C:20](=[O:21])[N:4]3[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]4[N:15]([NH2:16])[N:14]=[N:13][N:12]=4)[CH2:7][S:8][C@H:3]23)=[O:56])[N:53]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 13261994(6R,7R)-3-[(1-acetamidotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 133675107beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 88675957benzotriazol-1-yl (2Z)-2-butoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

Product 1

HCID 13261998(6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-butoxyimino-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 33.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (0.653 g, 2 mmol), triethylamine (0.405 mg, 4 mmol) and 1-benzotriazolyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-n-butoxyiminoacetate (1.32 g, 2.2 mmol) in dimethylacetamide (6 ml) and water (0.6 mol) 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-butoxyiminoacetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (0.535 g, 33.6%).

Sources & evidence

ORD record
ord-267a81cd058842d9b8fe9a828a393d23
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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