1,1'-(Diazomethylene)bis(benzene) → N-BOC allylglycine benzhydryl ester

HRID 2166751Notes

Reaction equation

HRID 2166751 reaction equation
[C:1]([CH:8]=[CH:9][CH2:10][NH:11][CH2:12][C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:16]1([C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N+]=[N-])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH:22]([O:14][C:13](=[O:15])[CH2:12][NH:11][CH2:10][CH:9]=[CH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 86738924N-BOC allylglycine

Product 1

HCID 86738923N-BOC allylglycine benzhydryl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-BOC allylglycine, 269 mg, is treated with 243 mg of diphenyldiazomethane in 25 ml of acetonitrile for one hour. The solvent is evaporated. Benzene is added, washed with aqueous NaHCO3 and brine, dried with MgSO4, filtered and evaporated, affording crystalline product which is washed with hexane and dried, 380 mg, m.p. 79° C.

Workup

  1. customThe solvent is evaporated
  2. additionBenzene is added
  3. washwashed with aqueous NaHCO3 and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customaffording crystalline product which
  8. washis washed with hexane
  9. customdried

Sources & evidence

ORD record
ord-10bafca9874c4c6f84f09a8d1c29de0f
Source dataset
uspto-grants-1983_06
Patent number
US04388475

Reaction notes

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