4-Methylmorpholine → HCID 66895618, compound

HRID 252695Notes

Reaction equation

HRID 252695 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][CH2:11][S:12][C:13]([F:16])([F:15])[F:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[F:35][C:36]1[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:37]=1[NH2:38]>C1COCC1.N#N>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]([C:17](=[O:19])[NH:38][C:37]1[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:36]=1[F:35])[CH2:10][CH2:11][S:12][C:13]([F:14])([F:15])[F:16])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 97092,4-DifluoroanilineHCID 62365Isobutyl chloroformateHCID 1633439HCID 1633439, compound

Product 1

HCID 66895618HCID 66895618, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 947NitrogenSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Boc-trifluoromethionine (212 mg, 0.851 mmol) was dissolved in dry THF in the presence of N2, and the temperature was adjusted to −78° C. Subsequently, N-methylmorpholine (0.11 ml, 1.000 mmol) was added thereto, and the mixture was stirred. Two minutes later, isobutyl chloroformate (0.13 ml, 0.999 mmol) was added thereto, and the mixture was stirred for 2 minutes. Finally, 2,4-difluoroaniline (0.10 ml, 0.982 mmol) was added thereto. TLC was performed to confirm disappearance of the starting compound, and the solid matters were filtered, followed by distillation of THF under reduced pressure. The residue was purified by column chromatography (Hex:AcOEt=80:20), thereby the product (191 mg, 54%) was obtained.

Workup

  1. customwas adjusted to −78° C
  2. stirringthe mixture was stirred for 2 minutes
  3. filtrationthe solid matters were filtered
  4. distillationfollowed by distillation of THF under reduced pressure
  5. customThe residue was purified by column chromatography (Hex:AcOEt=80:20)

Sources & evidence

ORD record
ord-f2936d3fa26d41feb5e6365b6b626cb2
Source dataset
uspto-grants-2011_01
Patent number
US07868206B2

Reaction notes

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