Ammonia → (+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide

HRID 585671Notes

Reaction equation

HRID 585671 reaction equation
C([N:3](CC)CC)C.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.N>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]([NH2:3])=[O:38])[CH2:31]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22337771(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxylic Acid

Product 1

HCID 22337819(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (16 μl) and isobutylchloroformate (14 μl) were added to a stirred solution of (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexanecarboxylic acid in anhydrous tetrahydrofuran (2 ml) at 0° C. under argon. After 30 min, aqueous ammonia solution (0.5 ml, 28% w/w) 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 (26 mg, 87%) as a mixture of diastereoisomers; m/z (ES+) 324 (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-5f1a8b38f2e2456a8c8c061ca6e35627
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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