Hydrochloric Acid → 3-{[(3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenyl ethylcarbamate

HRID 561888Notes

Reaction equation

HRID 561888 reaction equation
[CH2:1]([NH:3][C:4](=[O:54])[O:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[C:8]([CH2:17][N:18]([C:22](=[O:53])[CH:23]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][O:43][C:44]3[C:49]([Cl:50])=[CH:48][C:47]([CH3:51])=[CH:46][C:45]=3[Cl:52])=[CH:36][CH:35]=2)[CH2:24][NH:25]C(OC(C)(C)C)=O)[CH:19]2[CH2:21][CH2:20]2)[CH:7]=1)[CH3:2].Cl>C(Cl)Cl>[CH2:1]([NH:3][C:4](=[O:54])[O:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[C:8]([CH2:17][N:18]([C:22](=[O:53])[CH:23]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:40][CH2:41][CH2:42][O:43][C:44]3[C:45]([Cl:52])=[CH:46][C:47]([CH3:51])=[CH:48][C:49]=3[Cl:50])=[CH:38][CH:39]=2)[CH2:24][NH2:25])[CH:19]2[CH2:21][CH2:20]2)[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 667613853-{[(3-[(tert-Butoxycarbonyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenyl ethylcarbamate

Product 1

HCID 667621973-{[(3-Amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenyl ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.07 M) of 3-{[(3-[(tert-butoxycarbonyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl)(cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenyl ethylcarbamate from the previous step (1 eq.) was added HCl (4.0 M dioxane solution, 35 eq.). The resulting solution was stirred at RT for 3 h. Following the removal of the volatiles in vacuo, the resulting residue was directly subjected to column chromatography (SiO2, 94:6 (v/v) CH2Cl2:2.0 M NH3 in MeOH) to afford the title compound. MS (ESI+): 686.

Workup

  1. customthe removal of the volatiles in vacuo

Sources & evidence

ORD record
ord-eb05b55424474fd28d4c2fbfb9314126
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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