tert-Butyl isocyanate → N-(t-butylaminocarbonyl)-beta-phenyl isoserine methyl ester

HRID 381781Notes

Reaction equation

HRID 381781 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16].[N-]=C=O>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[CH:4]([OH:13])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:6][C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21]

Participants

5

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 105034IsocyanateHCID 10176516(2R,3S)-3-Phenylisoserine methyl ester

Product 1

HCID 22389502N-(t-butylaminocarbonyl)-beta-phenyl isoserine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2R,3S)-β-phenyl-isoserine methyl ester (4.35 g, 22 mM) is dissolved in dry THF (100 mL) and the flask cooled to 0°. To the mixture is added t-butyl isocyanate (2.8 mL, 25 mM). TLC after 15 minutes shows some starting material left so additional isocyanate (0.5 mL) is added. TLC after 1 hour shows no starting material so the solvent is concentrated under reduced pressure to give the title compound, NMR (CDCl3, TMS) 1.27, 3.43, 3.81, 4.34, 4.48, 5.27, 5.32, 7.29 and 7.34 δ; MS (FAB-High Res.) theory for C15H22N2O4+H=295.1658, found=295.1663.

Workup

  1. temperaturethe flask cooled to 0°
  2. additionis added
  3. waitTLC after 1 hour shows
  4. concentrationno starting material so the solvent is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e68aa05bd5be4b0d94993bc830cff8c9
Source dataset
uspto-grants-2001_10
Patent number
US06307064B1

Reaction notes

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