1-Bromoethyl acetate → 1-acetyloxyethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-3-methoxyprop-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 247757Notes

Reaction equation

HRID 247757 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[O:29][CH3:30])/[C:8]([NH:10][CH:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([OH:25])=[O:24])=[C:15](/[CH:18]=[CH:19]\[CH2:20][O:21][CH3:22])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[C:31]([O:34][CH:35](Br)[CH3:36])(=[O:33])[CH3:32]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[O:29][CH3:30])/[C:8]([NH:10][CH:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([O:25][CH:35]([O:34][C:31](=[O:33])[CH3:32])[CH3:36])=[O:24])=[C:15](/[CH:18]=[CH:19]\[CH2:20][O:21][CH3:22])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 111375051-Bromoethyl acetateHCID 88669300(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-3-methoxyprop-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 886689801-acetyloxyethyl (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-3-methoxyprop-1-enyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 43%

Procedure

Esterification of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-3-methoxy-1-propenyl]-3-cephem-4-carboxylic acid (300 mg, 0.66 mmole) with 1-bromoethyl acetate in a similar manner to that described in Example 10 gave the title compound (154 mg, 43%). Mp. 102°-105° C. (dec.). Estimated purity 95% (by HPLC, 1:1 CH3CN-pH 7 phosphate buffer).

Sources & evidence

ORD record
ord-23ab77e49c2e47e6a0ad73755e4e3694
Source dataset
uspto-grants-1987_11
Patent number
US04708955

Reaction notes

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