Hydrochloric Acid → HCID 131729088, compound

HRID 1670606Notes

Reaction equation

HRID 1670606 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[N+:20]([O-:22])=[O:21])[CH2:9]1)=O)(C)(C)C.[ClH:23]>O1CCOCC1.CCOCC>[ClH:23].[NH:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[N+:20]([O-:22])=[O:21])[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67335125HCID 67335125, compound

Product 1

HCID 131729088HCID 131729088, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Stir a solution of 3-(4-bromo-2-nitro-phenylamino)-azetidine-1-carboxylic acid tert-butyl ester (29.66 mmol, 11.04 g) in 4.0 M hydrogen chloride in dioxane (40 mL) at room temperature under nitrogen overnight. Solids crash out of solution. Dilute with ether (200 mL), filter off solids, rinse with ample ether and dry (8.54 g, 93%). 1H NMR (400 MHz, CD3OD): 4.12 (dd, 2H), 4.45 (dd, 2H), 4.72 (m, 1H), 6.76 (d, 1H), 7.62 (dd, 1H), 8.30 (d, 1H). LC-MS m/z (79Br/81Br) 272.0/274.0 [M+H]+.

Workup

  1. filtrationfilter off solids
  2. washrinse with ample ether
  3. customdry (8.54 g, 93%)

Sources & evidence

ORD record
ord-133f56ed00274b0a903cd5f5d362674f
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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