S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1) → HCID 11398716, compound
Reaction equation
[C:1]([NH:4][C@H:5]([C:27](O)=[O:28])[CH2:6][S:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].Cl.[C:31]([S:37][CH2:38][CH2:39][NH2:40])(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].Cl.C(SCCN)(=O)C.Cl.C(SCCN)(=O)C1C=CC=CC=1>C(Cl)Cl.CCOCC>[C:1]([NH:4][C@H:5]([C:27]([NH:40][CH2:39][CH2:38][S:37][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])[CH2:6][S:7][C:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The coupling reaction of 7 (7.4 mmol) with S-pivaloylcysteamine hydrochloride [(compound obtained according to the same methods as those described by T. Wieland and E. Bokelman, Ann. Chem., 1952, 576, 20-34, during the syntheses of S-acetylcysteamine hydrochloride and S-benzoylcysteamine hydrochloride) M.p.=212-213° C.] 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: CH2Cl2/ether 30%). 11 is collected in the form of a colorless foam with a yield of 86%. Rf (AcOEt/petroleum ether, 7/3): 0.5. [α]D20=+8.5° (c 1.29, CHCl3).
Workup
- customobtained
Sources & evidence
- ORD record
- ord-e465c681a8d34d5a95c0290db8cd52a5
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06989372B1
Reaction notes
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