S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1) → HCID 87919653, compound

HRID 1611649Notes

Reaction equation

[C:1]([NH:6][C@H:7]([C:29]([OH:31])=O)[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:36][CH2:37][CH2:38][NH2:39])(=[O:35])[CH3:34]>>[C:1]([NH:6][C@H:7]([C:29]([NH:39][CH2:38][CH2:37][S:36][C:33](=[O:35])[CH3:34])=[O:31])[CH2:8][S:9][C:10]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=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]([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 519453S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1)

HCID 57304755HCID 57304755, compound

Product 1

HCID 87919653HCID 87919653, compoundYield 67%

Procedure

The coupling reaction of 13 (3.93 mmol) with S-acetylcysteamine 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 60%). 14 is collected in the form of a colorless foam with a yield of 67%. Rf (AcOEt/petroleum ether, 6/4): 0.5. [α]D20=+9.3° (c 0.97, CHCl3).

Sources & evidence

ORD record: ord-f4ad23d3792b4d0f878a7cf89e4ca198
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989372B1

Reaction notes

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