4-Methylmorpholine → HCID 66894547, compound
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].CN1[CH2:26][CH2:25][O:24][CH2:23]C1.Cl[C:28](OCC(C)C)=[O:29].F[C:36]1C=C(F)[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]=[C:40]([O:29][CH3:28])[CH:26]=[C:25]([O:24][CH3:23])[CH:36]=1)[CH2:10][CH2:11][S:12][C:13]([F:14])([F:15])[F:16])([CH3:5])([CH3:6])[CH3:7]Participants
7
Procedure
N-Boc-trifluoromethionine (189 mg, 0.758 mmol) was dissolved in dry THF in the presence of N2, and the temperature was adjusted to −78° C. Subsequently, N-methylmorpholine (0.10 ml, 0.910 mmol) was added thereto, and the mixture was stirred. Two minutes later, isobutyl chloroformate (0.12 ml, 0.923 mmol) was added thereto, and the mixture was stirred for 2 minutes. Finally, 2,4-difluoroaniline (0.13 ml, 0.923 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 (236 mg, 86%) was obtained.
Workup
- customwas adjusted to −78° C
- stirringthe mixture was stirred for 2 minutes
- filtrationthe solid matters were filtered
- distillationfollowed by distillation of THF under reduced pressure
- customThe residue was purified by column chromatography (Hex:AcOEt=80:20)
Sources & evidence
- ORD record
- ord-6ecbd7e184bb400c9bcd0dddf6b8ec72
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868206B2
Reaction notes
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