Methanol → HCID 131728254, compound

HRID 2357111Notes

Reaction equation

HRID 2357111 reaction equation
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]=[CH:10][C:11]3[S:15][CH:14]=[N:13][C:12]=3[CH3:16])[CH2:7][S:8][C@H:3]12.O.CO.[CH:25]1([NH:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CC(C)=O>[CH:32]1([NH:31][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1.[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]=[CH:10][C:11]3[S:15][CH:14]=[N:13][C:12]=3[CH3:16])[CH2:7][S:8][C@H:3]12

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 7582DicyclohexylamineHCID 131715965HCID 131715965, compound

Product 1

HCID 131728254HCID 131728254, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 1.0 g quantity of 7-amino-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (E-isomer: 9% by HPLCb)) was suspended in a solvent mixture of 2 ml of water and 5 ml of methanol in a four-necked 100-ml flask. With addition of 0.68 ml of dicyclohexylamine, the suspension was stirred until crystals separated out from a transparent solution subsequently formed. The reaction mixture was allowed to stand at room temperature for 15 minutes and thereafter stirred for 15 minutes, and 7 ml of acetone was then slowly added to the mixture. The resulting mixture was subsequently cooled in an ice bath for 2 hours, and the resulting crystals were filtered off, washed with acetone and dried, affording 7-amino-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid dicyclohexylamine salt. While the filtration treatment in Examples was completed in about 1 minute, the filtration procedure in this comparative example required about 10 minutes.

Workup

  1. customseparated out from a transparent solution
  2. customsubsequently formed
  3. stirringstirred for 15 minutes
  4. temperatureThe resulting mixture was subsequently cooled in an ice bath for 2 hours
  5. filtrationthe resulting crystals were filtered off
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-163cd121653345caa29456835a671f02
Source dataset
uspto-grants-2010_07
Patent number
US07759483B2

Reaction notes

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