HCID 22253943, compound → HCID 86593962, compound

HRID 489882Notes

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:39][CH2:40][CH2:41][NH2:42])(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>>[C:1]([NH:6][C@H:7]([C:29]([NH:42][CH2:41][CH2:40][S:39][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[O:31])[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 22253943HCID 22253943, compound

HCID 57304755HCID 57304755, compound

Product 1

HCID 86593962HCID 86593962, compound

Procedure

The coupling reaction of 13 (3.93 mmol) of S-pivaloylcysteamine 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%). 16 is collected in the form of a foam which, after trituration in hexane, provides a colorless powder (Yd=88%). Rf (CH2Cl2/ether, 6/4): 0.82. M.p.=85-88° C. [α]D20=+5.9° (c 1.02, CHCl3).

Sources & evidence

ORD record: ord-28f3ec073e694b94aa3c9eb4fcd437d3
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979747B2

Reaction notes

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