Hydrochloric Acid → HCID 14052429, compound

HRID 2352088Notes

Reaction equation

HRID 2352088 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:62]/[O:63]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:27]([NH:29][CH:30]2[C:60](=[O:61])[N:32]3[C:33]([C:44]([O:46]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:45])=[C:34](/[CH:37]=[CH:38]/[CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C(O)=O>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:62]/[OH:63])/[C:27]([NH:29][CH:30]2[C:60](=[O:61])[N:32]3[C:33]([C:44]([OH:46])=[O:45])=[C:34](/[CH:37]=[CH:38]/[CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16166029HCID 16166029, compound

Product 1

HCID 14052429HCID 14052429, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(E)-3-acetoxy-1-propenyl)-3-cephem-4-carboxylate (1.98 g, 1.75 mmol) in formic acid (20 ml) was stirred for 2 hr at room temperature. Conc. hydrochloric acid (0.16 ml, 1.92 mmol) was added to the mixture and the mixture was stirred for 1 hr at room temperature. Filtration, and concentration of the filtrate, followed by trituration with IPE gave 975 mg of the crude product. Chromatography on a column of reversed phase silica gel and elution with 10% MeOH in water and concentration of the fraction containing the desired product gave 418 mg (51%) of the title compound as an amorphous powder. IR νmax (KBr) cm-1 1765, 1730, 1650. UV λmax (pH 7 phosphate buffer) nm (ε) 290 (23400). 1H NMR (DMSO-d6) δ 2.03 (3H, s, OAC), 3.65 (2H, ABq, 2-H), 4.61 (2H, ABq, CH2OAc), 5.15 (1H, d, J=5 Hz, 6-H), 5.75 (1H, dd, J=5 & 8 Hz, 7-H), 6.15 (1H, m, vinyl-H), 6.65 (1H, s, thiazole), 6.85 (1H, d, J=15 Hz, vinyl-H), 7.05 (2H, s, NH2).

Workup

  1. stirringthe mixture was stirred for 1 hr at room temperature
  2. filtrationFiltration, and concentration of the filtrate
  3. customgave 975 mg of the crude product
  4. washChromatography on a column of reversed phase silica gel and elution with 10% MeOH in water and concentration of the fraction
  5. additioncontaining the desired product

Sources & evidence

ORD record
ord-a33285bfd2e748a29a6e545fef2ff041
Source dataset
uspto-grants-1989_10
Patent number
US04874856

Reaction notes

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