Triethylamine → (S)-N-(1,4-dihydroxy-4-methylpentan-2-yl) morpholine-4-carboxamide

HRID 1916046Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][C:6]([CH3:9])([OH:8])[CH3:7])[CH2:3][OH:4].[N:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(N(CC)CC)C>ClCCl>[OH:4][CH2:3][C@@H:2]([NH:1][C:16]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:17])[CH2:5][C:6]([OH:8])([CH3:9])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-2-amino-4-methylpentane-1,4-diol (0.6 g, 4.5 mmol) was dissolved in anhydrous dichloromethane (10 mL) and the solution was cooled to 0° C. Next, 4-morpholinecarbonyl chloride (0.78 mL, 6.75 mmol) was added, followed by triethylamine (0.75 mL, 5.4 mmol). The reaction was stirred for 3 hrs at 0-5° C. The solvent was evaporated and the residue was purified using silica gel chromatography (10% methanol-dichloromethane) to afford Cmpd 66. Yield: 0.675 g (61%). MS (m/z): (M+H)=247.

Workup

customThe solvent was evaporated
customthe residue was purified
customto afford Cmpd 66

Sources & evidence

ORD record: ord-4d3c16d63cae4fd08ff848d96fd68bea
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618096B2

Reaction notes

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