S-(2-Aminoethyl) benzenecarbothioate--hydrogen chloride (1/1) → HCID 56984260, compound

HRID 1611652Notes

Reaction equation

[C:1]([NH:6][C@H:7]([C:29](O)=[O:30])[CH2:8][S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl.[C:33]([S:41][CH2:42][CH2:43][NH2:44])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[C:1]([NH:6][C@H:7]([C:29]([NH:44][CH2:43][CH2:42][S:41][C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:8][S:9][C:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 45048998S-(2-Aminoethyl) benzenecarbothioate--hydrogen chloride (1/1)

HCID 57304755HCID 57304755, compound

Product 1

HCID 56984260HCID 56984260, compound

Procedure

The coupling reaction of 13 (3.93 mmol) with S-benzoylcysteamine hydrochloride is carried out according to method B described in the first synthetic route (example 1). After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: AcOEt/petroleum ether 70%). 17 is collected in the form of a foam which, after trituration in hexane, provides a colorless foam (Yd=77%). Rf (CH2Cl2/ether, 6/4):0.76. [α]D20=+7.8° (c 1.03, CHCl3).

Sources & evidence

ORD record: ord-5156144096d344deaee88324fcab3f8a
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989372B1

Reaction notes

Loading…