Hydrochloric Acid → (3R)-ethyl 2-amino-3-ethyl-5-methylnon-8-enoate hydrochloride

HRID 523190Notes

Reaction equation

HRID 523190 reaction equation
C1(C(=[N:14][CH:15]([C@H:21]([CH2:29][CH3:30])[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:31]>C(OCC)C>[ClH:31].[NH2:14][CH:15]([C@H:21]([CH2:29][CH3:30])[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 86683257(3R)-ethyl 2-(diphenylmethyleneamino)-3-ethyl-5-methylnon-8-enoate

Product 1

HCID 86683258(3R)-ethyl 2-amino-3-ethyl-5-methylnon-8-enoate hydrochlorideYield 62.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (3R)-ethyl 2-(diphenylmethyleneamino)-3-ethyl-5-methylnon-8-enoate (7.00 g, 17.3 mmole) in diethyl ether (20 mL) was added aqueous 1.5 N HCl solutions (100 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 extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4; filtered; then concentrated under reduced pressure to get crude compound (2.6 g, 62.4%). The crude compound was taken to the next step without further purification. MS: MS m/z 242.4 (M++1).

Workup

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

Sources & evidence

ORD record
ord-67a621aae5d143ffb991fb448b27d6e6
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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