Hydrochloric Acid → HCID 24815984, compound

HRID 1669521Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([CH2:24][NH:25][OH:26])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.Cl.O1CCOCC1>>[ClH:23].[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)[CH2:24][NH:25][OH:26]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 86618211HCID 86618211, compound

Product 1

HCID 24815984HCID 24815984, compoundYield 132.1%

Procedure

To {(S)-2-[4-(4-chloro-phenoxy)-phenyl]-1-hydroxyaminomethyl-ethyl}-carbamic acid tert-butyl ester (18 mg, 0.046 mmol, 1 eq) in a 2 ml-vial was added 4 N HCl in dioxane (1 ml, 4 mmol, 86 eq.). The mixture was shaken at rt overnight. Then the volatile material was removed to give the desired product (10 mg, 74% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.94-3.01 (dd, J=6.8, 11.2 Hz, 1H), 3.01-3.05 (dd, J=5.2, 11.2 Hz, 1H), 3.17-3.20 (dd, J=2.4, 11.2 Hz, 1H), 3.37-3.42 (m, 1H), 3.80 (m, 1H), 7.02-7.05 (m, 4H), 7.34-7.35 (d, J=6.8 Hz, 2H), 7.43-7.45 (m, 2H); LCMS (UV, ESI), 294 (M+1), 87% purity.

Workup

customThen the volatile material was removed

Sources & evidence

ORD record: ord-3be5cdcbf82c41b783e32be2f39c9ffc
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989480B2

Reaction notes

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