Hydrochloric Acid → 7-[2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255774Notes

Reaction equation

HRID 255774 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:38][O:39][CH2:40][C:41]#[N:42])[C:10]([NH:12][CH:13]2[C:36](=[O:37])[N:15]3[C:16]([C:33]([OH:35])=[O:34])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO.O1CCCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:38][O:39][CH2:40][C:41]#[N:42])[C:10]([NH:12][CH:13]2[C:36](=[O:37])[N:15]3[C:16]([C:33]([OH:35])=[O:34])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1317153017-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153027-[2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 70.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.11 g.) and conc. hydrochloric acid (0.73 g.) in methanol (11 ml.) and tetrahydrofuran (5 ml.) was treated in a similar manner to that of Example 9-(2) to give 7-[2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.75 g.).

Sources & evidence

ORD record
ord-fe91541b953742eda50c4dea3691cbe2
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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