Phenylmethanesulfonyl chloride → HCID 59049296, compound

HRID 1264473Notes

Reaction equation

Cl.[NH:2]1[CH2:5][CH2:4][C@H:3]1[C:6]([O:8][CH3:9])=[O:7].[C:10]1([CH2:16][S:17](Cl)(=[O:19])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:9][O:8][C:6]([C@@H:3]1[CH2:4][CH2:5][N:2]1[S:17]([CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:19])=[O:18])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

(2S)-Methyl azetidine-2-carboxylate hydrochloride from Reference Example 1 (361.4 mg, 2.26 mmol, 1.0 eq) was dissolved in dry dichloromethane (10.0 mL) and treated with α-toluenesulfonyl chloride (458.1 mg, 2.40 mmol, 1.1 eq). After cooling to about 0° C. under argon atmosphere, diisopropylethylamine (420 μL, 2.41 mmol, 1.1 eq) was added and the reaction mixture was stirred at about room temperature overnight. The solvent was evaporated and the residue was subjected to flash chromatography (in dichloromethane) to give 431.2 mg (71 % yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 2.29-2.51 (m, 2H); 3.21-3.29 (m,1H); 3.81 (s, 3H); 4.02 (q,1H, J=8.6); 4.32 (d, 1H, J=9.4, 6.9); 4.46 (d, 1H, J=14.6); 4.86 (dd, 1H, J=9.4, 6.9); 7.34-7.43 (m, 3H); 7.46-7.54 (m, 2H).

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-c47480a112ee413785a28cbe7482b958
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544976B1

Reaction notes

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