Hydrochloric Acid → HCID 131729733, compound

HRID 1926706Notes

Reaction equation

HRID 1926706 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[O:6][C:7]1[CH:8]=[C:9]([C:16]([N+:19]([O-])=[O:20])=[CH:17][CH:18]=1)[CH2:10][C@@H:11]([C:13](O)=[O:14])[NH2:12])#[N:2].[ClH:25]>O1CCOCC1.CCOCC>[ClH:25].[NH2:12][C@H:11]1[CH2:10][C:9]2[C:16](=[CH:17][CH:18]=[C:7]([O:6][C:5]3[CH:4]=[C:3]([CH:24]=[CH:23][CH:22]=3)[C:1]#[N:2])[CH:8]=2)[N:19]([OH:20])[C:13]1=[O:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68781090HCID 68781090, compound

Product 1

HCID 131729733HCID 131729733, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

3-(3-Cyanophenoxy)-6-nitro-L-phenylalanine (87) N-(tert-Butoxycarbonyl)-3-(3-cyanophenoxy)-6-nitro-L-phenylalanine (86) (1.6 g, 3.8 mmol) was dissolved in a solution of HCl in dioxane (4 N, 70 mL). After 1.5 h, the reaction mixture was diluted with Et2O (200 mL) and filtered. The solid was washed with Et2O and dried at 50° C. under vacuum to afford the title compound as a white solid (1.3 g, 97%). LCMS m/z 328.1 (M+1). 1H NMR (400 MHz, CD3OD) δ 3.41 (dd, J=13.8, 7.5 Hz, 1H), 3.66 (dd, J=13.8, 7.4 Hz, 1H), 4.34 (t, J=7.4 Hz, 1H), 7.12-7.15 (m, 2H), 7.43-7.49 (m, 1H), 7.52-7.54 (m, 1H), 7.63-7.68 (m, 2H), 8.22-8.25 (m, 1H).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with Et2O
  3. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-9f4d0841b1914a16bdfd9a604d219e6f
Source dataset
uspto-grants-2012_05
Patent number
US08183238B2

Reaction notes

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