Citric Acid → HCID 131715471, compound

HRID 569142Notes

Reaction equation

HRID 569142 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[CH:18][CH:19]([CH3:21])[CH3:20])[C:15]([OH:17])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C@@H:23]1[C:52](=[O:53])[N:25]2[C:26]([C:36]([O:38][CH:39]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:37])=[C:27]([CH2:30][O:31][C:32](=[O:35])[NH:33][CH3:34])[CH2:28][S:29][C@H:24]12.CN1CCOCC1.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[CH:18][CH:19]([CH3:21])[CH3:20])[C:15]([NH:22][C@@H:23]2[C:52](=[O:53])[N:25]3[C:26]([C:36]([O:38][CH:39]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)=[O:37])=[C:27]([CH2:30][O:31][C:32](=[O:35])[NH:33][CH3:34])[CH2:28][S:29][C@H:24]23)=[O:17])[N:13]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 73910Diphenylphosphinic chlorideHCID 11744640HCID 11744640, compoundHCID 53794013HCID 53794013, compound

Product 1

HCID 131715471HCID 131715471, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoic acid (1.56 g), diphenylmethyl 7β-amino-3-methylcarbamoyloxymethyl-3-cephem-4-carboxylate (2.27 g), and N-methylmorpholine (2.0 ml) in dichloromethane (50 ml) is added diphenylphosphoryl chloride (1.27 g) at -30° C. After 2 hours, the reaction mixture is neutralized with 10% citric acid, washed, dried, and purified by chromatography give diphenylmethyl 7β-[2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino]-3-methylcarbamoyloxymethyl-3-cephem-4-carboxylate (2.27 g). Yield: 73%.

Workup

  1. washwashed
  2. customdried
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-d3ac6e9179fb48ab9aa1a2c77fb8fea3
Source dataset
uspto-grants-1988_03
Patent number
US04731362

Reaction notes

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