4-Methylmorpholine → HCID 86585966, compound

HRID 1369272Notes

Reaction equation

HRID 1369272 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-]>[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]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 3780918DiethylphosphiteHCID 10973860HCID 10973860, compound

Product 1

HCID 86585966HCID 86585966, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 25517Ammonium ChlorideSolvent

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(Ph3)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 magnessium sulfate, concentrated, and chromatographed over silica gel (5% MeOH/EtOAc) to an oil (0.2 g 37% yield). MS [M+H]+ 552 and [M+Na] 574.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over magnessium sulfate
  3. concentrationconcentrated
  4. customchromatographed over silica gel (5% MeOH/EtOAc) to an oil (0.2 g 37% yield)

Sources & evidence

ORD record
ord-baf94e6207cc4c5ca8ec740e6009864a
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

Loading…