Hydrochloric Acid → HCID 24815986, compound

HRID 1669524Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([CH2:24][N:25]([C:27](=[O:29])[CH3:28])[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>>[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][N:25]([OH:26])[C:27](=[O:29])[CH3:28]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 86618213HCID 86618213, compound

Product 1

HCID 24815986HCID 24815986, compoundYield 234.2%

Procedure

To a 40 ml vial was charged with {(S)-1-[(Acetyl-hydroxy-amino)-methyl]-2-[4-(4-chloro-phenoxy)-phenyl]-ethyl}-carbamic acid tert butyl ester (20 mg, 0.046 mmol, 1 eq.) followed by 4 N HCl (1 ml, 4 mmol, 86 eq.). The mixture was stirred at room temperature for 2 hr. The volatile material was removed under reduced pressure to give the desired product (20 mg, 100% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.02 (s, 3H), 2.83-2.87 (dd, J=6.4, 11.2 Hz, 1H), 3.17-3.20 (dd, J=4.8, 11.2 Hz, 1H), 3.46-3.87 (m, 4H), 7.0-7.03 (m, 4H), 7.32-7.33 (d, J=6.8 Hz, 2H), 7.42-7.44 (m, 2H), 8.06 (s, brs, 3H); LCMS (UV, ESI), 335 (M+1), 86% purity.

Workup

customThe volatile material was removed under reduced pressure

Sources & evidence

ORD record: ord-49a53841ddd44a8fa8adddede77ae901
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989480B2

Reaction notes

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