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

HRID 1739446Notes

Reaction equation

HRID 1739446 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

Conditions

Temperature
0 °C

Procedure

(2R,3S)-β-phenyl-isoserine methyl ester (4.35 g, 22 mM) is dissolved in 100 mL dry THF and the flask cooled to 0° C. To the solution is added t-butyl isocyanate (2.8 mL, 25 mM). TLC after 15 minutes shows some starting material left so another 0.5 mL of the isocyanate is added. TLC after 1 hour shows no starting material so the solvent is concentrated in vacuo leaving N-(t-butylaminocarbonyl)-β-phenyl isoserine methyl ester (3K).

Workup

  1. additionis added
  2. waitTLC after 1 hour shows
  3. concentrationno starting material so the solvent is concentrated in vacuo

Sources & evidence

ORD record
ord-e3733a47a51341cea714af40ec3c119c
Source dataset
uspto-grants-1999_10
Patent number
US05965739

Reaction notes

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