Triethylamine → HCID 21112788, compound

HRID 2373513Notes

Reaction equation

HRID 2373513 reaction equation
[NH2:1][C:2]([C:4]1([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:2]([C:4]1([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1)#[N:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 21112786HCID 21112786, compound

Product 1

HCID 21112788HCID 21112788, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(aminocarbonyl)tetrahydro-2H-pyran-4-yl-carbamate (C-25) and triethylamine (2.1 eq.) in dichloromethane was cooled to 0° C. and trifluoroacetic anhydride (1.1 eq.) was added dropwise under nitrogen. Stirring was continued for 1 hour allowing the mixture to reach room temperature. Volatiles were removed in vacuo and residue was taken up in ethyl acetate, washed with HCl 1N, brine and dried over Na2SO4. Evaporation gave a crude which was purified by flash chromatography on silica gel (eluent: petroleum ether: ethyl acetate=7:3) to give the title compound (C-26), colorless oil, as a 8:2 mixture of two rotamers by 1H NMR.

Workup

  1. customto reach room temperature
  2. customVolatiles were removed in vacuo and residue
  3. washwashed with HCl 1N, brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation
  6. customgave a crude which
  7. customwas purified by flash chromatography on silica gel (eluent: petroleum ether: ethyl acetate=7:3)

Sources & evidence

ORD record
ord-0451b53a1d9745cd8fe89a3a4edef370
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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