(S)-(2-(1-((tert-Butoxycarbonyl)amino)-2-methylpropyl)-5-chloropyridin-3-yl)methyl methanesulfonate → 1-(2-((S)-1-((tert-butoxycarbonyl)amino)-2-methylpropyl)-5-chloropyridin-3-yl)ethyl methanesulfonate

HRID 1777830Notes

Reaction equation

HRID 1777830 reaction equation
[CH3:1][S:2]([O:5][CH2:6][C:7]1[C:8]([C@@H:14]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:15]([CH3:17])[CH3:16])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)(=[O:4])=[O:3].[C:26](OC(=O)N[C@H](C1C(C(O)C)=CC(Cl)=CN=1)C(C)C)(C)(C)C>>[CH3:1][S:2]([O:5][CH:6]([C:7]1[C:8]([C@@H:14]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH:15]([CH3:17])[CH3:16])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)[CH3:26])(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 118274937(S)-(2-(1-((tert-Butoxycarbonyl)amino)-2-methylpropyl)-5-chloropyridin-3-yl)methyl methanesulfonateHCID 118282594tert-butyl((1S)-1-(5-chloro-3-(1-hydroxyethyl)pyridin-2-yl)-2-methylpropyl)carbamate

Product 1

HCID 1182749161-(2-((S)-1-((tert-butoxycarbonyl)amino)-2-methylpropyl)-5-chloropyridin-3-yl)ethyl methanesulfonate

Procedure

Procedure same as that for (S)-(2-(1-((tert-butoxycarbonyl)amino)-2-methylpropyl)-5-chloropyridin-3-yl)methyl methanesulfonate, using tert-butyl((1S)-1-(5-chloro-3-(1-hydroxyethyl)pyridin-2-yl)-2-methylpropyl)carbamate as a starting material. LC-MS tR=1.03 min in 1 min chromatography, MS (ESI) m/z 407.4 [M+H]+.

Sources & evidence

ORD record
ord-d6f5eaa85ab34ba8a89379d0d3359032
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

Loading…