Hydrochloric Acid → HCID 86683233, compound

HRID 1852175Notes

Reaction equation

HRID 1852175 reaction equation
C1(C(=[N:14][CH:15]([C@H:21]([CH3:29])[CH2:22][CH:23]([CH3:28])[CH2:24][CH2:25][CH:26]=[CH2:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.[ClH:30]>C(OCC)C>[ClH:30].[NH2:14][CH:15]([C@H:21]([CH3:29])[CH2:22][CH:23]([CH3:28])[CH2:24][CH2:25][CH:26]=[CH2:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86683231HCID 86683231, compound

Product 1

HCID 86683233HCID 86683233, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3R)-ethyl 2-((diphenylmethylene)amino)-3,5-dimethylnon-8-enoate (20 g) in diethyl ether (20 mL) was added aqueous 1.5 N HCl solution (200 mL) and the reaction mass was stirred at room temperature overnight. The reaction mass was washed with diethyl ether (100 mL). The aqueous solution was basified using saturated sodium bicarbonate solution and was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to get crude compound (3R)-ethyl 2-amino-3,5-dimethylnon-8-enoate hydrochloride (4 g, 30%). The crude compound was taken to the next step without further purification.

Workup

  1. washThe reaction mass was washed with diethyl ether (100 mL)
  2. extractionwas extracted with ethyl acetate (100 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cac3a7ba4e2b438fb551bb19ca53b04a
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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