Trimethylamine → HCID 86726492, compound

HRID 1487659Notes

Reaction equation

HRID 1487659 reaction equation
[OH:1][CH2:2][C@H:3]([NH:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([O:16][CH3:17])[CH:8]=1)[CH3:4].CN(C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C1COCC1>[CH3:23][S:24]([O:1][CH2:2][C@H:3]([NH:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([O:16][CH3:17])[CH:8]=1)[CH3:4])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 31297Methanesulfonyl chlorideHCID 86726493HCID 86726493, compound

Product 1

HCID 86726492HCID 86726492, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)—N-(1-hydroxypropan-2-yl)-3-methoxy-4-nitrobenzamide (1 equiv) in dry THF (0.2 M) was added trimethylamine (1.5 equiv) followed by addition of methanesulfonyl chloride (1.5 equiv). The reaction was stirred at room temperature overnight. The reaction mixture was washed with water (0.6 M) and brine (0.6 M) sequentially. The aqueous was extracted with ethyl acetate (0.23 M). The combined organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated. The crude material was purified by silica gel chromatography (20% ethyl acetate in petroleum ether) to afford the desired compound (62% yield). MS (ESI) m/z 253.1 [M+H]+.

Workup

  1. washThe reaction mixture was washed with water (0.6 M) and brine (0.6 M) sequentially
  2. extractionThe aqueous was extracted with ethyl acetate (0.23 M)
  3. dry with materialThe combined organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe crude material was purified by silica gel chromatography (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f372d334a94d4840ab7b7dd0a7429664
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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