Morpholine → HCID 60077772, compound

HRID 2084543Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30](F)=[CH:29][CH:28]=1)[C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:17])([CH3:16])[CH3:15]>CS(C)=O>[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([C:26](=[O:34])[C:27]1[CH:28]=[CH:29][C:30]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:31][CH:32]=1)[C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:15])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 120 °C

Procedure

Morpholine (1.41 mL, 16.2 mmol) and triethylamine (0.25 mL, 1.8 mmol) were added to a solution of [1(S)-(4-fluorobenzoyl)-2,2-dimethylpropyl]-carbamic acid tert-butyl ester (0.5 g, 1.62 mmol) in DMSO (8 mL), and the mixture heated at 120° C. for 15 hours. The solvent was removed in vacuo and the residual solid taken up in ethyl acetate (30 ml), and washed with 10% citric acid (aq.) (1×40 ml). The aqueous layer re-extracted with ethyl acetate (1×30 mL) and the combined organic phases were washed with brine (1×40 mL), dried over MgSO4, filtered and the solvent removed in vacuo to give a pale brown oil which was used without further purification (0.63 g, 100% crude).

Workup

customThe solvent was removed in vacuo
washwashed with 10% citric acid (aq.) (1×40 ml)
extractionThe aqueous layer re-extracted with ethyl acetate (1×30 mL)
washthe combined organic phases were washed with brine (1×40 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed in vacuo
customto give a pale brown oil which
customwas used without further purification (0.63 g, 100% crude)

Sources & evidence

ORD record: ord-13baf234b7584d4f9ae8b169ef635482
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716878B1

Reaction notes

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