Nitrogen → Methyl-[3-(2,2,2-trifluoro-acetylamino)-propyl]-carbamic acid isopropyl ester

HRID 870672Notes

Reaction equation

HRID 870672 reaction equation
N#N.[F:3][C:4]([F:14])([F:13])[C:5]([NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH3:12])=[O:6].CN1CCOCC1.Cl[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:26]([O:25][C:23](=[O:24])[N:11]([CH3:12])[CH2:10][CH2:9][CH2:8][NH:7][C:5](=[O:6])[C:4]([F:13])([F:14])[F:3])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 947NitrogenHCID 7917Isopropyl chloroformateHCID 79724-MethylmorpholineHCID 585874312,2,2-trifluoro-N-(3-(methylamino)propyl)acetamide

Product 1

HCID 86696374Methyl-[3-(2,2,2-trifluoro-acetylamino)-propyl]-carbamic acid isopropyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a rapidly stirred, 0° C., N2 blanketed, solution of 2,2,2-trifluoro-N-(3-methylamino-propyl)-acetamide (6.0 g, 32.4 mmol) and N-methylmorpholine [109-02-4] (7.1 mL, 64.6 mmol) in ethyl acetate (65 mL) was steadily added a 1.0M solution of isopropyl chloroformate in toluene (32.4 mL) over the course of 10 minutes. The reaction was allowed to stir and warm to ambient temperature over night at which time it was washed with brine, dried (MgSO4) and evaporated to provide 9.0 g of clear yellow oil. LRMS (ESI) m/z 271.1 [(M+H)]+, calc'd for C10H17F3N2O3: 270.25.

Workup

  1. stirringto stir
  2. temperaturewarm to ambient temperature over night at which time it
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-95e31ef2858845efa2a5994c6e65a2a5
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

Loading…