7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → 7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetyloxymethyl ester 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid butyryloxymethyl ester

HRID 839146

Reaction equation

HRID 839146 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([OH:13])=[O:12].C(OCC1CSC2N(C(=O)C2N)C=1C(O)=O)(=O)C.CC1CSC2N(C(=O)C2NC(=O)C(C2C=CC(CCl)=CC=2)N)C=1C(O)=O.[C:59]([O:65][CH2:66][O:67][C:68]([C:70]1[N:71]2[CH:74]([S:75][CH2:76][C:77]=1[CH3:78])[CH:73]([NH:79]C(=O)C(C1C=CC(CCl)=CC=1)N)[C:72]2=[O:92])=[O:69])(=[O:64])[C:60](C)(C)C>>[C:68]([O:67][CH2:66][O:12][C:11]([C:7]1[N:8]2[CH:3]([S:4][CH2:5][C:6]=1[CH3:14])[CH:2]([NH2:1])[C:9]2=[O:10])=[O:13])(=[O:69])[CH2:70][CH2:77][CH3:76].[C:59]([O:65][CH2:66][O:67][C:68]([C:70]1[N:71]2[CH:74]([S:75][CH2:76][C:77]=1[CH3:78])[CH:73]([NH2:79])[C:72]2=[O:92])=[O:69])(=[O:64])[CH3:60]

Participants

5

Reactant 4

HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 203258563-Methyl-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 538438393-Methyl-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester

Product 1

HCID 706226267-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid acetyloxymethyl ester 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid butyryloxymethyl ester

Procedure

When in the procedure of Example 16 an appropriate amount of 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid or the corresponding pivalyloxymethyl ester is substituted for 3-[(acetyloxy)-methyl]-7-amino-8-oxo-5-thia-1azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-methyl-7-[[2-[4-(chloromethyl)-phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid and 3-methyl-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester are obtained.

Workup

  1. customare obtained

Sources & evidence

ORD record
ord-41469ca47a804088918fe401be82849e
Source dataset
uspto-grants-1978_06
Patent number
US04093804

Linked notes

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