Hydrochloric Acid → HCID 57956086, compound

HRID 561864Notes

Reaction equation

HRID 561864 reaction equation
[CH:1]1([N:4]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([CH3:51])[C:46]=2[CH3:52])[C:5]([CH:7]([CH:17]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][C:35]3[C:40]([Cl:41])=[CH:39][C:38]([CH3:42])=[CH:37][C:36]=3[Cl:43])=[CH:27][CH:26]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:8][NH:9]C(=O)OC(C)(C)C)=[O:6])[CH2:3][CH2:2]1.Cl>C(Cl)Cl>[NH2:9][CH2:8][CH:7]([CH:17]([C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][O:34][C:35]2[C:40]([Cl:41])=[CH:39][C:38]([CH3:42])=[CH:37][C:36]=2[Cl:43])=[CH:29][CH:30]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[C:5]([N:4]([CH:1]1[CH2:3][CH2:2]1)[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH3:51])[C:46]=1[CH3:52])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86635930HCID 86635930, compound

Product 1

HCID 57956086HCID 57956086, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.03 M) of tert-butyl (2-{[cyclopropyl(2,3-dimethylbenzyl)amino]carbonyl}-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-4-pyridin-2-ylbutyl)carbamate from the previous step (1 eq.) was added HCl (4.0 M dioxane solution, 30 eq.). The resulting solution was stirred at RT for 4 h. Following the removal of the volatiles in vacuo, the resulting residue was directly loaded onto a SiO2 column packed with 95:5 (v/v) CH2Cl2:2.0 M NH3 in MeOH. Elution with the same solvent system furnished the title compound as a white froth. Diastereomer A: MS (ESI+): 646.0. Diastereomer B: MS (ESI+): 646.0.

Workup

  1. customthe removal of the volatiles in vacuo
  2. washElution with the same solvent system

Sources & evidence

ORD record
ord-c920455831d3474a9ec0943920a7833e
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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