HCID 70506324, compound → HCID 70506318, compound

HRID 1153725Notes

Reaction equation

HRID 1153725 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH:7]1[C:39](=[O:40])[N:9]2[C:10]([C:23]([O:25]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:24])=[C:11](/[CH:14]=[CH:15]/[S:16][C:17]3[N:21]([CH3:22])[N:20]=[N:19][N:18]=3)[CH2:12][S:13][C@H:8]12>O.C(O)=O>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[NH:6][CH:7]1[C:39](=[O:40])[N:9]2[C:10]([C:23]([OH:25])=[O:24])=[C:11](/[CH:14]=[CH:15]/[S:16][C:17]3[N:21]([CH3:22])[N:20]=[N:19][N:18]=3)[CH2:12][S:13][C@H:8]12

Participants

4

Reactant 1

HCID 70506324HCID 70506324, compound

Product 1

HCID 70506318HCID 70506318, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A solution of the hydrochloried/hydrofluoride salt of diphenylmethyl 7-(imidazol-2-yl)amino-3-[2-(1-methyltetrazol-5-ylthio)-trans-vinyl]ceph-3-em-4-carboxylate (300 mg.) in a mixture of water (2 ml.) and formic acid (2 ml.) was heated to 40°-45° for 1.75 hours. The solvent was evaporated and the residue dissolved in the minium amount of a mixture of CH2Cl2, methanol and water. Precipitation by addition of isopropanol gave 7-(imidazol-2-yl)amino-3-[2-(1-methyltetrazol-5-ylthio)-trans-vinyl]ceph-3-em-4-carboxylic acid as a salt (73 mg.) having the following n.m.r. in d6DMSO+CD3COOD: 3.62 (m, 2H); 3.90 (s, 3H); 5.1 (d, 1H); 5.5 (d, 1H); 6.7 (d, 1H); 7.2 (d, 1H); 6.75 (s, 2H).

Workup

  1. temperaturewas heated to 40°-45° for 1.75 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in the minium amount of a mixture of CH2Cl2, methanol and water
  4. customPrecipitation
  5. additionby addition of isopropanol

Sources & evidence

ORD record
ord-a7854ed9f3d0460f95378a69f83f7958
Source dataset
uspto-grants-1984_12
Patent number
US04486426

Reaction notes

Loading…