Ethyl Acetate → tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

HRID 1267008Notes

Reaction equation

HRID 1267008 reaction equation
CC1(C)N=C(/C=[CH:8]/[C:9]2[CH:14]=CC=C[CH:10]=2)OC1.Cl.C[NH:18][CH3:19].[C:20]([O-:23])(=[O:22])C.[Na+].[C:25]([BH3-])#N.[Na+].[C:29](OCC)(=[O:31])C>CO.CC(O)=O>[C:9]([O:23][C:20]([NH:18][C@H:19]([CH3:25])[CH:29]=[O:31])=[O:22])([CH3:14])([CH3:10])[CH3:8]

Participants

8

Reactant 5

HCID 8857Ethyl AcetateHCID 10473Dimethylamine, hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 6311587Oxazole, 4,5-dihydro-4,4-dimethyl-2-(2-phenylethenyl)-

Product 1

HCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2-(R)-[N-(tert-Butoxycarbonyl)amino]propanal was prepared from D-alanine Me-ester hydrochloride according to the procedure described in the literature (Chakravarty et al, J. Med. Chem 1989, p1886). A mixture of the aldehyde (16.21 g), dimethylamine hydrochloride (15.28 g), sodium acetate( 1.53 g) and sodium cyanoborohydride (8.24 g) in methanol (250 mL) was stirred at room temperature for 18 hours maintaining pH at 6-7 with AcOH. The reaction mixture was dissolved in ethyl acetate, washed with water, dried (MgSO4), and the solvent removed in vacuo to yield a viscous oil which was purified using flash chromatography to yield the dimethylamino derivative as a white solid (10.81 g).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto yield a viscous oil which
  5. customwas purified

Sources & evidence

ORD record
ord-9bb96c61aace429fad5ae6e619e7bf8d
Source dataset
uspto-grants-2003_04
Patent number
US06552021B2

Reaction notes

Loading…