S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1) → HCID 516560, compound

HRID 1611644Notes

Reaction equation

HRID 1611644 reaction equation
[C:1](N[C@H](C(O)=O)CSC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:3])[CH3:2].Cl.[C:31]([S:36][CH2:37][CH2:38][NH2:39])(=[O:35])[CH:32]([CH3:34])[CH3:33].Cl.[C:41]([S:44][CH2:45][CH2:46][NH2:47])(=[O:43])[CH3:42].Cl.[C:49](SCCN)(=[O:56])C1C=CC=CC=1.[CH2:61](Cl)Cl.CCOCC>>[C:1]([NH:39][C@H:38]([C:49]([NH:47][CH2:46][CH2:45][S:44][C:41](=[O:43])[CH3:42])=[O:56])[CH2:37][S:36][C:31](=[O:35])[C:32]([CH3:61])([CH3:34])[CH3:33])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 519453S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1)HCID 7408363HCID 7408363, compoundHCID 21881112Ethyl ether methylene chlorideHCID 22253953HCID 22253953, compoundHCID 45048998S-(2-Aminoethyl) benzenecarbothioate--hydrogen chloride (1/1)

Product 1

HCID 516560HCID 516560, compoundYield 80%

Procedure

The coupling reaction of 7 (4.5 mmol) with S-isobutyrylcysteamine 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.=147-148° 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%). 10 is collected in the form of a colorless foam with a yield of 80%. Rf (AcOEt/petroleum ether, 8/2): 0.37. [α]D20=+10° (c 1.1, CHCl3).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-52085b210826408e9e71a539277db754
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

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