Hydrochloric Acid → HCID 131733182, compound

HRID 1526774Notes

Reaction equation

[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:6]([OH:28])=[C:7]([C@@H:9]([NH:16][C:17](=[O:27])[CH2:18][NH:19]C(OC(C)(C)C)=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=1.C(#N)C>O1CCOCC1>[ClH:1].[NH2:19][CH2:18][C:17]([NH:16][C@H:9]([C:7]1[CH:8]=[C:3]([Br:2])[CH:4]=[C:5]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:6]=1[OH:28])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

4M HCl in 1,4-dioxane (3.0 mL) was added to a solution of a crude sample of (S)-ethyl 3-(5-bromo-3-(tert-butyl)-2-hydroxyphenyl)-3-(2-((tert-butoxycarbonyl)amino)acetamido)propanoate (0.922 g, 1.84 mmol) in 1,4-dioxane (3.0 mL) at 0° C. (ice-bath) and the reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 30 min. The reaction mixture was then heated at 50° C. for 2.5 h under nitrogen atmosphere to give a yellow-orange suspension. The solvent was evaporated in-vacuo to afford a dirty yellow-orange foamy solid. Acetonitrile (25 mL) was added to the solid, stirred for 5 min to give a cream-yellow suspension and evaporated in vacuo to afford a dirty cream solid (0.935 g). LC/MS analysis of the product shows the desired product's mass: m/z 402 (79BrM+H) and m/z 404 (81BrM+H), Calcd for C17H25BrN2O4: 401.29.

Workup

waitat room temperature for 30 min
temperatureThe reaction mixture was then heated at 50° C. for 2.5 h under nitrogen atmosphere
customto give a yellow-orange suspension
customThe solvent was evaporated in-vacuo
customto afford a dirty yellow-orange foamy solid
stirringstirred for 5 min
customto give a cream-yellow suspension
customevaporated in vacuo

Sources & evidence

ORD record: ord-6ee099e74aa043df936cf1d3f86b12e5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085606B2

Reaction notes

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