Hydrochloric Acid → HCID 86685802, compound

HRID 2361589Notes

Reaction equation

HRID 2361589 reaction equation
C1(C(=[N:14][CH:15]([C@H:21]([CH3:29])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:28])[CH:26]=[CH2:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.Cl>C(OCC)C>[NH2:14][CH:15]([C@H:21]([CH3:29])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:28])[CH:26]=[CH2:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86685800HCID 86685800, compound

Product 1

HCID 86685802HCID 86685802, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3R)-ethyl 2-(diphenylmethyleneamino)-3,7 dimethylnon-8-enoate (14.5 g, 37 mmol) in diethyl ether (25 mL) was added aqueous 1.5 N HCl solution (125 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 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude compound (2.1 g, 23%). The crude compound was taken to the next step without further purification. 1H NMR (400 MHz, CDCl3): δ ppm 5.85-5.60 (m, 1H), 4.98-4.85 (dd, J=1.6, 2.8 Hz, 2H), 4.10-4.06 (m, 2H), 3.15-3.14 (m, 1H), 2.15-2.02 (m, 1H), 1.94-1.75 (m, 3H), 1.32-1.17 (m, 9H), 0.95-0.93 (m, 3H), 0.84-0.74 (m, 3H). MS: MS m/z 227.7 (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 layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff2c34844b894acd90e83b63b3a194e4
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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