Hydrochloric Acid → HCID 86720268, compound

HRID 1754310Notes

Reaction equation

HRID 1754310 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([C:12]([O:14][C@H:15]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[CH2:16][C:17]2[C:22]([Cl:23])=[CH:21][N+:20]([O-:24])=[CH:19][C:18]=2[Cl:25])=[O:13])[CH2:9]1)=O)(C)(C)C.Cl.C(OCC)C.C(#N)C>C(OCC)(=O)C>[ClH:23].[Cl:25][C:18]1[CH:19]=[N+:20]([O-:24])[CH:21]=[C:22]([Cl:23])[C:17]=1[CH2:16][C@H:15]([O:14][C:12]([CH:10]1[CH2:11][NH:8][CH2:9]1)=[O:13])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 86720270HCID 86720270, compound

Product 1

HCID 86720268HCID 86720268, compoundYield 200.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (S)-4-(2-((1-(tert-butoxycarbonyl)azetidine-3-carbonyl)oxy)-2-(3,4-dimethoxyphenyl)ethyl)-3,5-dichloropyridine 1-oxide (105 mg, 0.2 mmol) in ethyl acetate (0.5 mL) was added a 2M solution of HCl in diethyl ether (1.5 mL, 3 mmol). The mixture was allowed to stir at room temperature for 4 hours and then acetonitrile (5 mL) was added. The mixture was allowed to stir at room temperature for 3 hours. The solid was removed by filtration, washed with diethyl ether and dried to afford the title compound as a yellow solid (93 mg, 95%).

Workup

  1. stirringto stir at room temperature for 3 hours
  2. customThe solid was removed by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-c9340d857c134e309825cf3d48d42d44
Source dataset
uspto-grants-2015_10
Patent number
US09169245B2

Reaction notes

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