Methanesulfonamide → HCID 89545437, compound

Participants

Role	Name	HCID	Charge
Reactant	Methanesulfonamide	HCID 72879	—
Reactant	Propan-2-ol--water (1/1)	HCID 21889133	—
Reactant	1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine	HCID 51003674	—
Reactant	HCID 117613621	HCID 117613621	—
Product	HCID 89545437	HCID 89545437	—

Reaction Steps

(2R,3S)-Ethyl 2,3-dihydroxy-3-(1-(4-((5-(trifluoromethyl)pyridin-2-yl)oxy)-phenyl)-1H-indol-3-yl)propanoate (4) was prepared as follows: A mixture of compound 3 (0.12 g, 1.0 eq), Ad-Mix-α (1.5 eq, Aldrich), and MeSO2NH2 (Aldrich, 1.2 eq) in 10 mL of i-PrOH/water (1/1) was shaken at room temperature for 4 hours. The reaction was quenched with EtOAc/water (60 mL/20 mL). The organic layer was separated, washed with brine, concentrated and purified by column (EtOAc/hexanes 5/4) to give compound 4 as a colorless oil (80 mg): 1H-NMR (400 MHz, CDCl3) δ: 8.42 (s, 1H), 8.05 (s, 1H), 7.89 (1H, dd, 2.6 & 8.7 Hz), 7.77-7.8 (m, 1H), 7.5-7.57 (m, 3H), 7.18-7.28 (m, 4H), 7.04 (d, 1H, 8.8 Hz), 6.9 (s, 1H), 6.28 (d, 1H, 1.5 Hz), 4.36 (q, 2H, 7.1 Hz), 1.37 (t, 3H, 7.2 Hz).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181185B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-8d66a00555c84b91b6960094de569553
Source note	uspto-grants-2015_11