Water → HCID 21353535, compound

HRID 1660704Notes

Reaction equation

HRID 1660704 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[C@H:10]([CH3:12])[OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:16]I.O>CN(C=O)C>[CH3:16][O:14][C:13](=[O:15])[C@H:9]([C@H:10]([CH3:12])[OH:11])[NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 6992538(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanoic acid

Product 1

HCID 21353535HCID 21353535, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-Boc-L-allo-threonine (500 mg, 2.28 mmol) in DMF (5 mL), KHCO3 (637 mg, 4.56 mmol) and MeI (227 μl, 3.65 mmol) were added and the reaction was stirred 5 h at rt. Water (20 mL) was added and the mixture was extracted with ether (3×20 mL), dried (Na2SO4) and evaporated to afford the methyl ester 106 (494 mg, 93%) that was used without purification in the next step. 1H-NMR (500 MHz, CDCl3): 1.19-1.25 (m, 3H), 1.48 (s, 9H), 3.78 (s, 3H), 4.05-4.10 (m, 1H), 4.32-4.40 (m, 1H), 4.45-4.54 (m, 1H).

Workup

  1. extractionthe mixture was extracted with ether (3×20 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-e9f1addf8a0545328c948588fd9217fe
Source dataset
uspto-grants-2011_10
Patent number
US08030279B2

Reaction notes

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