S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1) → HCID 11284496, compound

HRID 1611646Notes

Reaction equation

HRID 1611646 reaction equation
[C:1]([NH:4][C@H:5]([C:27]([OH:29])=O)[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(SCCN)(=O)C.Cl.[C:39]([S:47][CH2:48][CH2:49][NH2:50])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl.CCOCC>[C:1]([NH:4][C@H:5]([C:27]([NH:50][CH2:49][CH2:48][S:47][C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:29])[CH2:6][S:7][C:8]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 519453S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1)HCID 7408363HCID 7408363, compoundHCID 45048998S-(2-Aminoethyl) benzenecarbothioate--hydrogen chloride (1/1)

Product 1

HCID 11284496HCID 11284496, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

The coupling reaction of 7 (7.41 mmol) is carried out according to Method B described in the first synthetic route (example 1): S-acetylcysteamine hydrochloride was replaced by S-benzoylcysteamine hydrochloride (T. Wieland and E. Bokelman, Ann. Chem., 1952, 576, 20-34. After the various treatments, the expected compound is isolated by flash chromatography on a silica gel column (eluent: CH2Cl2/ether 15%). 12 is collected in the form of a colorless foam with a yield of 62%. Rf (AcOEt/petroleum ether, 7/3): 0.42. [α]D20=+10.8° (c 1.11, CHCl3).

Sources & evidence

ORD record
ord-6cb7cf923b2c4590a1cfc93d8b5bfb80
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

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