Acetic Acid → HCID 14349717, compound

HRID 1607711Notes

Reaction equation

HRID 1607711 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:26])[C@H:10]2[NH:14][C:15](=[S:25])[NH:16][C:17]([O:19][CH2:20][C:21](Cl)([Cl:23])[Cl:22])=[O:18])[C:7]=1[C:27]([O:29][CH:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])(=[O:3])[CH3:2].C(O)(=O)C.P([O-])(O)(O)=O.[K+]>[Zn].O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:26])[C@H:10]2[NH:14][C:15]([NH2:16])=[S:25])[C:7]=1[C:27]([O:29][CH:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])(=[O:3])[CH3:2].[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:26])[C@H:10]2[NH:14][C:15]([NH:16][C:17]([O:19][CH2:20][CH:21]([Cl:22])[Cl:23])=[O:18])=[S:25])[C:7]=1[C:27]([O:29][CH:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:28])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 516951Monobasic potassium phosphateHCID 86743374HCID 86743374, compound

Product 2

HCID 14349717HCID 14349717, compoundHCID 86743373HCID 86743373, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.16 g of (6R-trans)-3-[(acetyloxy)methyl]-8-oxo-7-[[thioxo[[(2,2,2-trichloroethoxy)carbonyl]amino]methyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester, 660 mg of zinc dust, 0.25 ml of glacial acetic acid, 2 ml of 1M aqueous potassium dihydrogen phosphate and 10 ml of tetrahydrofuran was stirred for 1 hour and then filtered. The filtrate was subjected to flash chromatography, eluting with ethyl acetate:petroleum ether in a 1:1 to 1:2 gradient, giving 340 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[(aminothioxomethyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester and 30 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[[[[(2,2-dichloroethoxy)carbonyl]amino]thioxomethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester.

Workup

  1. filtrationfiltered
  2. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d4a9e43cec134390a13ad0d2283e6386
Source dataset
uspto-grants-1989_09
Patent number
US04866169

Reaction notes

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