Diethylamine methanol → (s)-3-Nitro-4-((tetrahydro-2h-pyran-3-yl)methylamino)benzenesulfonamide

HRID 2167953Notes

Reaction equation

HRID 2167953 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][O:14][CH2:13]1)([O-:3])=[O:2].CO.C(NCC)C>C(=O)=O>[N+:1]([C:4]1[CH:5]=[C:6]([S:18]([NH2:21])(=[O:19])=[O:20])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][O:14][CH2:13]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 21877050Diethylamine methanolHCID 67126530(r)-3-Nitro-4-((tetrahydro-2h-pyran-3-yl)methylamino)benzenesulfonamide

Product 1

HCID 67126407(s)-3-Nitro-4-((tetrahydro-2h-pyran-3-yl)methylamino)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

The racemic mixture of EXAMPLE 11A was resolved by chiral SFC on an AD column (21 mm i.d.×250 mm in length) using a gradient of 10-30% 0.1% diethylamine methanol in CO2 over 15 minutes (oven temperature: 40° C.; flow rate: 40 mL/minute) to provide the title compound.

Workup

  1. customover 15 minutes
  2. custom(oven temperature: 40° C.; flow rate: 40 mL/minute)

Sources & evidence

ORD record
ord-6f275eac60f94bdebab5d8ac01c85a34
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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