Trifluoroacetic acid → HCID 178463445, compound

HRID 335496Notes

Reaction equation

HRID 335496 reaction equation
[CH3:1][S:2]([O:5][C@@H:6]1[C@H:11]2[N:12]=[C:13]([N:15](C(OC(C)(C)C)=O)[CH2:16][CH3:17])[S:14][C@H:10]2[O:9][C@@H:8]2[CH2:25][O:26]C(C3C=CC=CC=3)[O:28][C@@H:7]12)(=[O:4])=[O:3].FC(F)(F)C(O)=O.CO.C(Cl)Cl>C(Cl)Cl>[CH3:1][S:2]([O:5][C@@H:6]1[C@H:11]2[N:12]=[C:13]([NH:15][CH2:16][CH3:17])[S:14][C@H:10]2[O:9][C@H:8]([CH2:25][OH:26])[C@H:7]1[OH:28])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 86731577HCID 86731577, compound

Product 1

HCID 178463445HCID 178463445, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3aR,4aR,8aR,9R,9aR)-2-[(tert-butoxycarbonyl)(ethyl)amino]-7-phenyl-3a,4a,5,8a,9,9a-hexahydro[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d][1,3]thiazol-9-yl methanesulfonate (30.00 mg; 0.06 mmol; 1.00 eq.) in DCM (100.00 μl) was added trifluoroacetic acid (10.00 μl; 0.13 mmol; 2.31 eq.). The reaction was stirred at room temperature for 3 h. The desired product was isolated by flash chromatography (KPNH, 0 to 50% MeOH/DCM). To afford (3aR,5R,6R,7R,7aR)-2-(ethylamino)-6-hydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-7-yl methanesulfonate (19.2 mg, 64%) as a white solid (once lyophilized).

Sources & evidence

ORD record
ord-10767cb59b474c42b117128769f37af1
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

Loading…