Triethylamine → tert-butyl N-(1-cyano-1-methylethyl)carbamate

HRID 632012Notes

Reaction equation

HRID 632012 reaction equation
[NH2:1][C:2](=O)[C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:5])[CH3:4].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:2]([C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:5])[CH3:4])#[N:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11287144tert-Butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamate

Product 1

HCID 18316698tert-butyl N-(1-cyano-1-methylethyl)carbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-amino-2-methyl-1-oxopropan-2-ylcarbamate (Example 12 a, 12.5 g) and triethylamine (CAN 121-44-8, 29 g) in methylene chloride (150 mL) was added trifluoroacetic acid anhydride (CAN 407-25-0, 27.2 g) dropwise at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 4 h. After that the mixture was washed with water, 5 N citric acid and brine, the organic phase was dried over anhydrous sodium sulfate and concentrated to give the title compound (11 g, 97%) as a yellow solid; MS: m/e=207.1 [M+Na]+.

Workup

  1. washAfter that the mixture was washed with water, 5 N citric acid and brine
  2. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-959127d0cb744d73b20c8f8036c86f25
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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