Benzene → HCID 66584299, compound

HRID 2415528Notes

Reaction equation

HRID 2415528 reaction equation
[C:1]([O:9][CH:10]([O:14][C:15]([NH:17][CH2:18][C:19]1([CH2:25][C:26]([OH:28])=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:16])[CH:11]([CH3:13])[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[C:1]([O:9][CH:10]([O:14][C:15]([NH:17][CH2:18][C:19]1([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:16])[CH:11]([CH3:12])[CH3:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 11959210HCID 11959210, compound

Product 1

HCID 66584299HCID 66584299, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-{[(α-benzoyloxyisobutoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid (84) (150 mg, 0.38 mmol), benzene (18 mL), and methanol (2 mL) was cooled to 0° C. Trimethylsilyldiazomethane was added slowly at 0° C. until the yellow color persisted. The mixture was stirred at 0° C. for 30 min until the reaction was complete (monitored by TLC). After removing the solvent under reduced pressure, chromatography of the residue on silica gel, eluting with 5% ethyl acetate/hexane gave 98 mg (64%) of the title compound.

Workup

  1. customAfter removing the solvent under reduced pressure, chromatography of the residue on silica gel
  2. washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7ee9fa7ad74046d1b490bdae9577115c
Source dataset
uspto-grants-2004_11
Patent number
US06818787B2

Reaction notes

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