Methanesulfonyl chloride → HCID 19003119, compound

HRID 2259293Notes

Reaction equation

Cl.[NH2:2][CH:3]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)=[O:5].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>>[CH3:26][S:27]([NH:2][CH:3]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1)=[O:5])(=[O:29])=[O:28]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 19003122HCID 19003122, compound

Product 1

HCID 19003119HCID 19003119, compound

Procedure

Following the method of Example 18, 3,5-dimethylbenzyl 2-amino-3-(3-indolyl)propionate hydrochloride and methanesulphonylchloride gave the title compound which was recrystallised from ethyl acetate/petroleum ether, m.p. 96°-97° C. 1H NMR (360 MHz, CDCl3) δ8.18 (1H, s), 7.70 (1H, d, J=7 Hz), 7.48 (1H, d, J=7 Hz), 7.37 (1H, t, J=7 Hz), 7.28 (1H, t, J=7 Hz), 7.12 (1H, s), 7.08 (1H, s), 6.98 (2H, s), 5.04 (2H, s), 4.89 (1H, d, J=9.2 Hz), 4.50 (1H, m), 3.32 (2H, d, J=5.7 Hz), 2.72 (3H, s), 2.30 (6H, s). Found: C, 62.6; H, 5.9; N, 6.8. C21H24N2O4S requires C, 63.0; H, 6.0; N, 7.0.

Sources & evidence

ORD record: ord-eace5ee13d1b45d6af8ccfb3f1bf4aed
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05472978

Reaction notes

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