Hydrochloric Acid → HCID 131729090, compound

HRID 1670635Notes

Reaction equation

HRID 1670635 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])[C@@H:11]([OH:26])[CH2:10]1)=O)(C)(C)C>O1CCOCC1.ClCCl>[ClH:1].[Br:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C@H:12]2[CH2:13][CH2:14][NH:9][CH2:10][C@@H:11]2[OH:26])=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67335296(3S,4S)-4-(4-Bromo-2-nitro-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131729090HCID 131729090, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4 M hydrogen chloride in dioxane (90 mL) slowly to a solution of (3S,4S)-4-(4-bromo-2-nitro-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.035 mol, 14.6 g) in dry dichloromethane (50 mL) at room temperature and stir for 16 h. Filter the precipitate and dry under vacuum to obtain the title compound (9.84 g, 80%) as a yellow solid.

Workup

  1. filtrationFilter the precipitate
  2. customdry under vacuum

Sources & evidence

ORD record
ord-d8dc6c10e3a14072823fd7cb1fa5f6b2
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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