Pyridine → (S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(2-methyl-N-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)thiazole-5-carboxamido)propanamido)propanoate

HRID 628130Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][CH2:8][C@H:9]([NH:20][C:21](=[O:35])[C@@H:22]([NH:26][CH2:27][C:28]1[O:29][C:30](=[O:34])[O:31][C:32]=1[CH3:33])[CH2:23][O:24][CH3:25])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:36][C:37]1[S:38][C:39]([C:42](O)=[O:43])=[CH:40][N:41]=1.N1C=CC=CC=1>C(Cl)Cl.Cl>[CH3:6][O:7][CH2:8][C@H:9]([NH:20][C:21](=[O:35])[C@@H:22]([N:26]([CH2:27][C:28]1[O:29][C:30](=[O:34])[O:31][C:32]=1[CH3:33])[C:42]([C:39]1[S:38][C:37]([CH3:36])=[N:41][CH:40]=1)=[O:43])[CH2:23][O:24][CH3:25])[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

Referring to FIG. 38, phosphorous oxychloride (323 μL, 3.46 mmol) was added dropwise to (S)-benzyl 3-methoxy-2-((S)-3-methoxy-2-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)amino)propanamido)propanoate (1.46 g, 3.46 mmol), 2-methylthiazole-5-carboxylic acid (248 mg, 3.46 mmol) and pyridine (1.07 mL, 10 mmol) in DCM (20 ml) at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, diluted with 1N HCl, and extracted with DCM. The organic layer was separated, dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography to give the product as a white solid (346 mg, 22%).

Workup

extractionextracted with DCM
customThe organic layer was separated
dry with materialdried (Na2SO4)
customevaporated
customThe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-c2cca2cd9e9e438f9ecfea57fa0d2c0e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309283B2

Reaction notes

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