3-Heptanone → 2-(s)-(1-Propyl-butylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide

HRID 131656

Reaction equation

Cl.C[O:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH2:21])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9].[CH3:25][CH2:26][C:27](=O)[CH2:28][CH2:29][CH2:30][CH3:31].S([O-])([O-])(=O)=O.[Na+].[Na+].C([BH3-])#N.[Na+]>ClC(Cl)C.CO.C(O)(=O)C>[OH:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH:21][CH:28]([CH2:29][CH2:30][CH3:31])[CH2:27][CH2:26][CH3:25])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt (100 mg, 0.265 mmol) and 3-heptanone (0.1 mL), acetic acid (0.2 mL), sodium sulfate and sodium cyanoborohydride (100 mg) in dichloroethane (2 mL) and methanol (1 mL) was stirred at 40° C. overnight. The mixture was quenched with water, basified by dilute sodium hydroxide, and extracted with methylene chloride. The organic layer was concentrated to dryness. The residue was purified by Biotage silica gel column chromatography to isolate 2-(S)-(1-propyl-butylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide as a colorless oil, LC-MS, RT=2.2 min, M+1=426.5.

Workup

customThe mixture was quenched with water
extractionextracted with methylene chloride
concentrationThe organic layer was concentrated to dryness
customThe residue was purified by Biotage silica gel column chromatography

Sources & evidence

ORD record: ord-59679df6d87c47658f1cf87b4a0d71bc
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384968B2

Linked notes

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