Hydrochloric Acid → HCID 131715306, compound

HRID 255777Notes

Reaction equation

HRID 255777 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:32][O:33][CH2:34][CH2:35][Br:36])[C:10]([NH:12][CH:13]2[C:30](=[O:31])[N:15]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[S:23][CH:24]=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.O1CCCC1>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:32][O:33][CH2:34][CH2:35][Br:36])[C:10]([NH:12][CH:13]2[C:30](=[O:31])[N:15]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[S:23][CH:24]=[N:25][N:26]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 131715307HCID 131715307, compound

Product 1

HCID 131715306HCID 131715306, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N.M.R. δ(DMSO-d6, ppm): 3.3-3.9 (4H, m), 4.1-4.8 (4H, m), 5.23 (1H, d, J=5Hz), 5.84 (1H, dd, J=5 Hz, 9 Hz), 7.63 (1H, s), 8.72 (1H, s), 9.57 (1H, s), 9.71 (1H, d, J=9 Hz), 12.71 (1H, broad s). (2) A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-bromoethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.5 g.), conc. hydrochloric acid (0.99 g.), tetrahydrofuran (10 ml.) and methanol (22 ml.) was treated in similar manner to that of Example 9 (2), to give 7-[2-(2-aminothiazol-4-yl)-2-(2-bromoethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.15 g.).

Sources & evidence

ORD record
ord-44837b4aa78a4ec8ab2545fb8438b73c
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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