Triethylamine → Benzyl 2-{[(trifluoroacetyl)amino]methyl}morpholine-4-carboxylate

HRID 1371378Notes

Reaction equation

HRID 1371378 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][NH:9][CH2:8]1)=[O:4].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CO>[F:14][C:2]([F:13])([F:1])[C:3]([NH:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([C:23]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:24])[CH2:8]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 115502612,2,2-trifluoro-N-(morpholin-2-ylmethyl)acetamide

Product 1

HCID 17984666Benzyl 2-{[(trifluoroacetyl)amino]methyl}morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

To a stirred solution of Intermediate 1 (6.37 g) in methanol (250 ml) under nitrogen was added benzylchloroformate (4.7 ml) and triethylamine (6.3 ml). The mixture was stirred at 22° C. for 1 h before the volatiles were removed in vacuo. The residue was purified by Biotage flash chromatography on a 90 g silica cartridge eluting with 33% ethyl acetate in cyclohexane, to give the title compound as a white solid (4.4 g).

Workup

  1. customwere removed in vacuo
  2. customThe residue was purified by Biotage flash chromatography on a 90 g silica cartridge
  3. washeluting with 33% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-568a120fde3c436e8fe42518c432a810
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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