Ethyl 2-(diphenylmethyleneamino)acetate → HCID 86683231, compound

HRID 1852174Notes

Reaction equation

HRID 1852174 reaction equation
CC1C=CC(S(O[C@H:12]([CH2:14][CH:15]([CH3:20])[CH2:16][CH2:17][CH:18]=[CH2:19])[CH3:13])(=O)=O)=CC=1.[CH2:21]([O:23][C:24](=[O:40])[CH2:25][N:26]=[C:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:22].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1(C)C=CC=CC=1>[C:28]1([C:27](=[N:26][CH:25]([C@H:12]([CH3:13])[CH2:14][CH:15]([CH3:20])[CH2:16][CH2:17][CH:18]=[CH2:19])[C:24]([O:23][CH2:21][CH3:22])=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 2733832Lithium HexamethyldisilazideHCID 86683232HCID 86683232, compound

Product 1

HCID 86683231HCID 86683231, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (2S)-4-methyloct-7-en-2-yl 4-methylbenzenesulfonate (54 g, 0.182 moles) and N-(diphenylmethylene)glycinate ethyl ester (48.7 g, 0.182 moles) in toluene (500 mL) was added LiHMDS (36.5 g, 0.218 moles, 1 M solution in THF) at 0° C. The reaction mass was allowed to come to room temperature and was then heated at 110° C. for 2 h. The reaction mass was cooled to room temperature, quenched with water and extracted with ethyl acetate (200 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to get crude compound (3R)-ethyl 2-((diphenylmethylene)amino)-3,5-dimethylnon-8-enoate (75 g). The crude compound was taken to the next step without further purification.

Workup

  1. customto come to room temperature
  2. temperatureThe reaction mass was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with ethyl acetate (200 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f58766aa2db9403b82f216805b78d1ac
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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