L-Homoserine → HCID 131729812, compound

HRID 1512018Notes

Reaction equation

HRID 1512018 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].N12CCCN=C1CCCCC2.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(#N)C>[Si:20]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 12647L-HomoserineHCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 131729812HCID 131729812, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of L-homoserine (1 g, 8.4 mmol) in acetonitrile (10 ml) at 0° C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.32 ml, 8.8 mmol, 1.05 eq). tert-butyldimethylsilyl chloride (1.33 g, 8.8 mmol, 1.05 eq) was then added portionwise over 5 minutes and the reaction mixture allowed to warm to room temperature and stirred for 16 hours. A white precipitate formed, which was filtered off and washed with acetonitrile before drying under reduced pressure. The title compound was isolated as a white solid (1.8 g, 92% yield). 1H NMR (500 MHz, DMSO-d6), δ: 7.5 (1H, br s), 3.7 (1H, m), 3.35 (4H, br m), 1.95 (1H, m), 1.70 (1H, m), 0.9 (9H, s), 0.1 (6H, s).

Workup

  1. customA white precipitate formed
  2. filtrationwhich was filtered off
  3. washwashed with acetonitrile
  4. custombefore drying under reduced pressure

Sources & evidence

ORD record
ord-bf7cc01357864e808d7b9f158cf716ad
Source dataset
uspto-grants-2012_07
Patent number
US08217050B2

Reaction notes

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