1,1'-Carbonyldiimidazole → (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

HRID 2171263Notes

Reaction equation

HRID 2171263 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]([O:17][C:18]([NH:20][C@H:21]([C:23]([OH:25])=O)[CH3:22])=[O:19])([CH3:16])([CH3:15])[CH3:14].Cl.[CH3:27][O:28][NH:29][CH3:30]>ClCCl.C(N(CC)CC)C>[CH3:27][O:28][N:29]([CH3:30])[C:23](=[O:25])[C@@H:21]([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:14])([CH3:15])[CH3:16])[CH3:22]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateYield 96.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

CDI (185.6 g) was added to a dichloromethane (2000 ml) solution containing N-(tert-butoxycarbonyl)-L-alanine (200 g) at 5° C. or less, followed by stirring for 1 hour. Subsequently, triethylamine (115.8 g) and N-methoxy-N-methylamine hydrochloride (111.7 g) were added to the solution, followed by stirring at 15° C. or less for 1.5 hours. Dichloromethane (230 ml) was added to the reaction solution. The organic layers were washed with a 20% sodium hydroxide aqueous solution and the solvent was distilled away under reduced pressure. Heptane was added to the obtained residue for suspension and a solid was collected by filtration. A white solid of (S)-tert-butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (237.8 g) was thus obtained.

Workup

  1. stirringby stirring at 15° C. or less for 1.5 hours
  2. washThe organic layers were washed with a 20% sodium hydroxide aqueous solution
  3. distillationthe solvent was distilled away under reduced pressure
  4. additionHeptane was added to the obtained residue for suspension
  5. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-f9232e9b997d4a32b9e6ddbd7d655b05
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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