Ethylamine → (+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-ethylcyclohexanecarboxamide

HRID 585673Notes

Reaction equation

HRID 585673 reaction equation
[CH2:1]([N:3](CC)CC)[CH3:2].C(OC(Cl)=O)C(C)C.[CH3:16][O:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH2:27][O:28][CH3:29])[CH:23]=[CH:22][C:21]=1[CH:30]1[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([OH:38])=O)[CH2:31]1.C(N)C>O1CCCC1>[CH3:16][O:17][CH2:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH2:27][O:28][CH3:29])[CH:23]=[CH:22][C:21]=1[CH:30]1[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([NH:3][CH2:1][CH3:2])=[O:38])[CH2:31]1

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22337771(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxylic Acid

Product 1

HCID 22337779(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-ethylcyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (11 μl) and isobutylchloroformate (10 μl) were added to a stirred solution of (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexanecarboxylic acid in anhydrous tetrahydrofuran (2 ml) under argon at 0° C. After 30 min, ethylamine (0.5 ml, 2M solution in tetrahydrofuran) was added. The reaction mixture was partitioned between water (20 ml) and ethyl acetate (50 ml). The aqueous layer was extracted with ethyl acetate (2×20 ml) and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to give the title compound as a solid (24 mg, quant.) and a mixture of diastereoisomers; m/z (ES+) 352 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between water (20 ml) and ethyl acetate (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×20 ml)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b113bc4cf3ce4a06baa689a030d644b5
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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