tert-Butanol → Tert-butyl 2-{[(benzyloxy)carbonyl]amino}-2-cyanoacetate

HRID 426021Notes

Reaction equation

HRID 426021 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:16]#[N:17])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](O)([CH3:21])([CH3:20])[CH3:19].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:16]#[N:17])[C:13]([O:15][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 189427342-{[(Benzyloxy)carbonyl]amino}-2-cyanoacetic acid

Product 1

HCID 18942739Tert-butyl 2-{[(benzyloxy)carbonyl]amino}-2-cyanoacetateYield 67.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-benzyloxycarbonylamino-2-cyanoacetic acid (2.00 g, 8.54 mmol), toluene (20 ml) and t-butyl alcohol (6.33 g, 85.4 mmol), was added trifluoroacetic acid anhydride (7.17 g, 34.2 mmol) dropwise and the solution was stirred for half an hour. The reaction solution was neutralized by adding 10% NaOH aqueous solution (18 g), the organic layer was separated and washed with water three times, dried over sodium sulfate, insoluble materials were filtered and the filtrate was condensed to give t-butyl 2-benzyloxycarbonylamino-2-cyanoacetate (1.67 g, yield 67.4%) as a pale yellow oil.

Workup

  1. customthe organic layer was separated
  2. washwashed with water three times
  3. dry with materialdried over sodium sulfate, insoluble materials
  4. filtrationwere filtered
  5. customcondensed

Sources & evidence

ORD record
ord-08dd7447126a4e6fabbea96663f686ba
Source dataset
uspto-grants-2012_01
Patent number
US08106230B2

Reaction notes

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