Hydrochloric Acid → (3S,7S,8R,9S)-8-(isobutyryloxy)-9-methyl-7-(naphthalen-1-ylmethyl)-2-oxo-1,5-dioxonan-3-aminium chloride

HRID 708994Notes

Reaction equation

HRID 708994 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C@@H:9]1[C:17](=[O:18])[O:16][C@@H:15]([CH3:19])[C@H:14]([O:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[C@@H:13]([CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH2:12][O:11][CH2:10]1)=O)(C)(C)C.[ClH:44].O1CCOCC1>C(Cl)Cl>[Cl-:44].[C:21]([O:20][C@H:14]1[C@H:15]([CH3:19])[O:16][C:17](=[O:18])[C@@H:9]([NH3+:8])[CH2:10][O:11][CH2:12][C@@H:13]1[CH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)(=[O:25])[CH:22]([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 117974254[(3S,6S,7R,8S)-3-[bis(tert-butoxycarbonyl)amino]-6-methyl-8-(1-naphthylmethyl)-4-oxo-1,5-dioxonan-7-yl]2-methylpropanoate

Product 1

HCID 117974668(3S,7S,8R,9S)-8-(isobutyryloxy)-9-methyl-7-(naphthalen-1-ylmethyl)-2-oxo-1,5-dioxonan-3-aminium chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(3S,6S,7R,8S)-3-[bis(tert-butoxycarbonyl)amino]-6-methyl-8-(1-naphthylmethyl)-4-oxo-1,5-dioxonan-7-yl]2-methylpropanoate (260 mg, 0.434 mmol) in CH2Cl2 (1 mL) was added 4 M HCl in dioxane (2.17 mL, 8.67 mmol) slowly (gas evolution) and the resulting solution was stirred at room temperature for 2.5 h. The solvent was evaporated under a stream of N2 to give (3S,7S,8R,9S)-8-(isobutyryloxy)-9-methyl-7-(naphthalen-1-ylmethyl)-2-oxo-1,5-dioxonan-3-aminium chloride as a white powder. The powder was dried under high vacuum for 20 h to remove residual HCl and was used without further purification for the amide picolinamide formation: ESIMS m/z 400 ([M+H]+).

Workup

  1. customThe solvent was evaporated under a stream of N2

Sources & evidence

ORD record
ord-a05d3c9098744232a40952185f06959e
Source dataset
uspto-grants-2015_11
Patent number
US09179674B2

Reaction notes

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