L-Alanine → tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

HRID 719183Notes

Reaction equation

HRID 719183 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=O)[CH3:3].CC1(C)N=C(/C=[CH:14]/[C:15]2[CH:20]=CC=C[CH:16]=2)OC1.Cl.CNC.[C:26]([O-:29])(=[O:28])C.[Na+].C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C.ClCCl>[C:15]([O:29][C:26]([NH:1][C@@H:2]([CH3:3])[CH:4]=[O:6])=[O:28])([CH3:14])([CH3:16])[CH3:20]

Participants

9

Reactant 5

HCID 5950L-AlanineHCID 10473Dimethylamine, hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 6311587Oxazole, 4,5-dihydro-4,4-dimethyl-2-(2-phenylethenyl)-

Product 1

HCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(S)-[N-(tert-Butoxycarbonyl)amino]propanal was prepared from L-alanine according to the procedure described in the literature (Chakravarty et al, J. Med. Chem 1989, p1886). A mixture of the aldehyde (2.62 g), dimethylamine hydrochloride (2.47 g), sodium acetate (1.99 g) and sodium cyanoborohydride (1.43 g) in methanol (45 mL) was stirred at room temperature for 8 hours. The reaction mixture was dissolved in ethyl acetate, washed with water, dried (MgSO4), and the solvent removed in vacuo to yield a viscous oil. This was dissolved in dichloromethane, extracted with citric acid, basified with sodium hydroxide, and re-extracted with ethyl acetate. The organic layer was reduced in vacuo to yield the dimethylamino derivative as a white solid (586 mg).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto yield a viscous oil
  5. extractionextracted with citric acid
  6. extractionre-extracted with ethyl acetate

Sources & evidence

ORD record
ord-74a5981dbac04d8fac2eafc3967aff12
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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