HCID 22253953, compound → HCID 86593960, compound

HRID 489880Notes

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:38][CH2:39][CH2:40][NH2:41])(=[O:37])[CH:34]([CH3:36])[CH3:35]>>[C:1]([NH:6][C@H:7]([C:29]([NH:41][CH2:40][CH2:39][S:38][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])=[O:31])[CH2:8][S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 22253953HCID 22253953, compound

HCID 57304755HCID 57304755, compound

Product 1

HCID 86593960HCID 86593960, compoundYield 75%

Procedure

The coupling reaction of 13 (3.93 mmol) with S-isobutyrylcysteamine 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 65%). 15 is collected in the form of a colorless foam with a yield of 75%. Rf (AcOEt/petroleum ether, 5/5): 0.6. [α]D20=+7.9° (c 1.27, CHCl3).

Sources & evidence

ORD record: ord-f885f31b8cb64c25a9c3a7bf6f6a1810
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979747B2

Reaction notes

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