L-Homoserine → HCID 57699948, compound

HRID 1009958Notes

Reaction equation

HRID 1009958 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].N12CCCN=C1CCCCC2.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>C(#N)C>[NH2:1][C@@H:2]([CH2:3][CH2:4][O:5][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

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

Product 1

HCID 57699948HCID 57699948, 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). Tert-butyl-dimethyl-silyl chloride (1.33 g, 8.8 mmol) 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 had formed which was filtered off and washed with acetonitrile before drying under vacuum. The title compound was isolated as a white solid (1.8 g, 92%). 1H NMR (300 MHz, DMSO), δ: 7.50 (1H, bs), 3.70 (1H, m), 3.35 (4H, bm), 1.95 (1H, m), 1.70 (1H, m), 0.90 (9H, s), 0.10 (6H, s).

Workup

  1. customA white precipitate had formed which
  2. filtrationwas filtered off
  3. washwashed with acetonitrile
  4. custombefore drying under vacuum

Sources & evidence

ORD record
ord-bcd9cee912294ec6a33a8c9e673bf234
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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