Ethyl 2-(diphenylmethyleneamino)acetate → HCID 86685800, compound

HRID 2361588Notes

Reaction equation

CC1C=CC(S(O[CH:12]([CH2:14][CH2:15][CH2:16][CH:17]([CH3:20])[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][CH2:15][CH2:16][CH:17]([CH3:20])[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

Conditions

Temperature: 110 °C

Procedure

To a solution of 2R)-6-methyloct-7-en-2-yl 4-methylbenzenesulfonate (15 g, 50.6 mmol) and N-(diphenylmethylene)glycinate ethyl ester (13.53 g, 50.6 mmol) in toluene (120 mL) was added LiHMDS (60.7 mL, 60.7 mmol, 1M solution in THF) at 0° C. The reaction mass was allowed to come to room temperature 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 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude compound (14.5 g). The crude compound was taken to the next step without further purification. MS: MS m/z 392.1 (M++1).

Workup

customto come to room temperature
temperatureThe reaction mass was cooled to room temperature
customquenched with water
extractionextracted with ethyl acetate (200 mL×3)
dry with materialThe combined organic layer was dried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-24d368df52fb47a6963bfa27e30127c4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691757B2

Reaction notes

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