4-Methylmorpholine → HCID 86585272, compound

HRID 1241348Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[C:14](OS(C(F)(F)F)(=O)=O)[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[P:32]([O-:39])([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35].CN1[CH2:46][CH2:45][O:44]CC1>C(#N)C.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:34]([O:33][P:32]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:15][C:14]=1[P:32]([O:44][CH2:45][CH3:46])([O:33][CH2:34][CH3:35])=[O:36])(=[O:39])[O:36][CH2:37][CH3:38])[CH3:35]

Participants

Conditions

Temperature: 90 °C

Procedure

Trifluoro-methanesulfonic acid 5-(tert-butoxycarbonylamino-methyl)-2-trifluoromethanesulfonyloxy-phenyl ester (5 g, 10.0 mmol), diethyl phosphite (2.8 mL, 20.3 mmol), N-methylmorpholine (2.7 mL, 25.1 mmol) and tetrakis(triphenylphosphine)-palladium(0) (1.2 g) were dissolved in anhydrous acetonitrile (100 mL) and heated in a sealed tube at 90° C. for 48 h. After cooling, the mixture was diluted with EtOAc (200 mL) and washed with water, 1 N HCl and brine. The organic layer was dried over magnesium sulfate, concentrated, and purified by silica gel chromatography (5% MeOH/CHCl3) to yield the product as a colorless oil (2.0 g, 42%). 1H NMR (300 Mhz, CDCl3) δ 1.35 (m, 12 H), 3.79 (bs, 2 H), 3.96 (m, 8H), 7.45 (m, 1H), 7.91 (m, 2H).

Workup

temperatureAfter cooling
washwashed with water, 1 N HCl and brine
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated
custompurified by silica gel chromatography (5% MeOH/CHCl3)

Sources & evidence

ORD record: ord-433feed1f6d2431ea2035c5152bb454e
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115589B2

Reaction notes

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