Hydrochloric Acid → 3-(4-((Benzyloxycarbonylamino)methyl)piperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 216069Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:26](=[O:40])[NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35](=[O:39])[N:36]([CH3:38])[CH3:37])[CH:29]=2)[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>CO>[CH3:37][N:36]([CH3:38])[C:35](=[O:39])[O:34][C:30]1[CH:31]=[CH:32][CH:33]=[C:28]([NH:27][C:26]([C:13]2([CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:40])[CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl 4-((benzyloxycarbonylamino)methyl)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)-piperidine-1-carboxylate from step C (0.245 g, 0.441 mmol) in MeOH (2 mL) was added 4 M HCl in dioxane (0.331 mL, 1.32 mmol). The reaction was heated at 50° C. for 1 hour, and then concentrated under vacuum, re-dissolved in MeOH and re-concentrated twice to give the title compound as the hydrochloride salt. MS (ES+) [M+H]+=455.

Workup

concentrationconcentrated under vacuum
dissolutionre-dissolved in MeOH
concentrationre-concentrated twice

Sources & evidence

ORD record: ord-fa11a199854243a38238d9f5a10a129e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193202B2

Reaction notes

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