4-Methylmorpholine → N-(1(S)-carbomethoxy-3-methylthiopropyl)3-chloromethylbenzamide

HRID 1901585Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH2:8][S:9][CH3:10])[NH2:6].CN1[CH2:18][CH2:17][O:16]CC1.[Cl:19][C:20]1[C:21]([CH3:29])=[C:22]([CH:26]=[CH:27]C=1)C(Cl)=O>C(Cl)Cl>[C:4]([C@@H:5]([NH:6][C:17](=[O:16])[C:18]1[CH:27]=[CH:26][CH:22]=[C:21]([CH2:20][Cl:19])[CH:29]=1)[CH2:7][CH2:8][S:9][CH3:10])([O:3][CH3:2])=[O:11]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of (S) methionine methyl ester hydrochloride (10.56 g, 52.9 mmol) and 4-N-methylmorpholine (21.34 g, 211.6 mmol) under nitrogen in 200 mL of methylene chloride at 0° C. was added 3-chloro-methyl benzoyl chloride (10.00 g, 52.9 mmol) dropwise via syringe. After addition the cooling bath was removed and the resulting solution was stirred for 16 h at 20° C. The methylene chloride solution was extracted with 125 mL each of water, 2% potassium hydrogen sulfate, saturated sodium hydrogen carbonate, and saturated sodium chloride. The methylene chloride was dried over magnesium sulfate and concentrated in vacuo to the title compound as an oil. 1HNMR (300 MHz, CDCl3)δ 7.85 (1H, s), 7.76 (1H, d, J=8 Hz), 7.56 (1H, d, J=8 Hz), 7.45 (1H, t, J=8 Hz), 6.96 (1H, d, J=7 Hz), 4.94 (1H, q, J=5 Hz), 4.62 (2H, s), 3.81 (3H, s), 2.60 (2H, t, J=8 Hz), 2.30 (1H, m), 2.15 (1H, m), 2.12 (3H, s).

Workup

additionAfter addition the cooling bath
customwas removed
extractionThe methylene chloride solution was extracted with 125 mL each of water, 2% potassium hydrogen sulfate, saturated sodium hydrogen carbonate, and saturated sodium chloride
dry with materialThe methylene chloride was dried over magnesium sulfate
concentrationconcentrated in vacuo to the title compound as an oil

Sources & evidence

ORD record: ord-4697761f357e451facbaefed5d88f51f
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578629

Reaction notes

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