Water → tert-butyl N-((1S)-1-cyanoethyl)carbamate

HRID 452036Notes

Reaction equation

HRID 452036 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]([CH3:12])[C:9]([NH2:11])=O)([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]([C:9]#[N:11])[CH3:12])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 7015295Boc-Ala-NH2

Product 1

HCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamateYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl[(1S)-2-amino-1-methyl-2-oxoethyl]carbamate (Step 1, 0.7 g, 0.004 mol) in N,N-dimethylformamide (5 mL) was added 343 mg of cyanuric chloride (0.00186 mol) at once. The reaction mixture was stirred for 4 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with EtOAc in hexane (30-50%) to yield the desired product (400 mg, 63%). 1H-NMR (300 MHz, DMSO-d6): 7.74 (d, J=7.0 Hz, 1H), 4.48 (m, 1H), 1.40 (s, 9H), 1.35 (d, J=7.0 Hz, 3H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a silica gel column with EtOAc in hexane (30-50%)

Sources & evidence

ORD record
ord-e23b8298f3a748a7b362acbe3f79ff7f
Source dataset
uspto-grants-2013_07
Patent number
US08487096B2

Reaction notes

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