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

HRID 585672Notes

Reaction equation

HRID 585672 reaction equation
C(N(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.[NH2:39][OH:40]>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:39][OH:40])=[O:38])[CH2:31]1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22337771(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxylic Acid

Product 1

HCID 22337757(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-hydroxycyclohexanecarboxamide

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) at 0° C. under argon. After 30 min, aqueous hydroxylamine solution (0.5 ml, 50 wt %) 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 (26 mg, quant.) and a mixture of diastereoisomers; m/z (ES+) 340 (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-e0f382662fef46a48c73c03e4abb08e1
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

Loading…