Diethyl Ether → HCID 54551191, compound

HRID 845844Notes

Reaction equation

HRID 845844 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:23])[C@H:10]2[NH:14][C:15]2[S:16][C:17]([C:20](=[O:22])[CH3:21])=[CH:18][N:19]=2)[C:7]=1[C:24]([O:26]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.CCOCC>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:23])[C@H:10]2[NH:14][C:15]2[S:16][C:17]([C:20](=[O:22])[CH3:21])=[CH:18][N:19]=2)[C:7]=1[C:24]([OH:26])=[O:25])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86742288HCID 86742288, compound

Product 1

HCID 54551191HCID 54551191, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 255 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[(5-acetyl-2-thiazolyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester was reacted with anisole and trifluoroacetic acid in dichloromethane with stirring at 0° C. for 30 minutes, then at room temperature for 30 minutes. The addition of ether and petroleum ether gave a precipitate which was washed with ether, giving 135 mg of the desired product as a pale yellow powder.

Workup

  1. waitat room temperature for 30 minutes
  2. customgave a precipitate which
  3. washwas washed with ether

Sources & evidence

ORD record
ord-13138c7cb69b4acf8f9e6fec552eb7e5
Source dataset
uspto-grants-1988_07
Patent number
US04760140

Reaction notes

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