Acetic Acid → HCID 15853247, compound

HRID 1850105Notes

Reaction equation

HRID 1850105 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([O:12][CH3:15])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 15853247HCID 15853247, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-methylpropanoic acid (10.03 g, 49.4 mmol) in MeOH/DCM (60 mL/140 mL) at room temperature was added drop wise (trimethylsilyl)diazomethane (37.0 mL, 74.0 mmol). The reaction mixture was stirred for 30 minutes. Acetic acid was added drop wise to quench (trimethylsilyl)diazomethane. The reaction mixture was concentrated under reduced pressure to afford the desired product as a white solid (10.56 g). LCMS m/z 240.2 (M+Na)+, Rt 0.71 min.

Workup

  1. customto quench (trimethylsilyl)diazomethane
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1478a2a021324e7b80d4918fd2ea5f3e
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…