4-Methylmorpholine → HCID 86585966, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH:4]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](OS(C(F)(F)F)(=O)=O)=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=1.[P:37]([O-:44])([O:41][CH2:42][CH3:43])[O:38][CH2:39][CH3:40].CN1[CH2:51][CH2:50][O:49]CC1>CC#N.[NH4+].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:36])[CH:4]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([P:37]([O:41][CH2:42][CH3:43])([O:38][CH2:39][CH3:40])=[O:44])=[C:8]([P:37]([O:49][CH2:50][CH3:51])([O:38][CH2:39][CH3:40])=[O:41])[CH:7]=1Participants
7
Conditions
- Temperature
- 95 °C
Procedure
To 3-(3,4-bis-trifluoromethanesulfonyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (2 g, 3.47 mmol), diethyl phosphite (1 mL, 7.65 mmol) and 4-methyl morpholine (0.93 mL, 8.3 mmol) in MeCN (10 ml) was added Pd(PPh3)4 (167 mg, 0.15 mmol). The mixture was allowed to stirred for two days at 95° C. then diluted with saturated NH4Cl and extracted with EtOAc. The organic layer was dried over magnesium sulfate, concentrated, and chomatographed over silica gel (5% MeOH/EtOAc) to an oil (0.2 g, 37% yield). MS [M+H]+ 552 & [M+Na] 574.
Workup
- extractionextracted with EtOAc
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9cee471cde874b759bc9903660838c82
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573295B2
Reaction notes
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