Hydrochloric Acid → HCID 87249126, compound

Reaction equation

[OH:1][C@@H:2]1[C@H:6]2[N:7](C(OC(C)(C)C)=O)[CH2:8][C@@H:9]([O:10][S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C@H:5]2[O:4][CH2:3]1.O1CCOCC1.[ClH:34]>>[ClH:34].[CH3:18][C:17]1[CH:19]=[CH:20][C:14]([S:11]([O:10][C@@H:9]2[CH2:8][NH:7][C@@H:6]3[C@@H:2]([OH:1])[CH2:3][O:4][C@H:5]23)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 59343397(3R,3aR,6R,6aS)-tert-Butyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate

Product 1

HCID 87249126HCID 87249126, compound

Procedure

Boc alcohol (35b) (11.0 g, 27.6 mmol) was dissolved in 4N HCl in dioxan (100 mL, 400 mmol) and the mixture stirred at ambient temperature for 1 hour. The mixture was then concentrated in vacuo and azeotroped three times from toluene to give a pale brown solid (Yield 9.25 g). HPLC-MS 3001 [M+H]+; δH (500 MHz, d6-DMSO) 2.44 (3H, s, CH3-aryl), 3.13 (1H, dd, J=7.8 Hz, NHCH2), 3.38 (1H, dd, J=6.7 Hz, NHCH2), 3.68 (1H, dd, J=2.0, 9.9 Hz, CHOCH2), 3.93 (1H, d, J=5.3 Hz, NHCHCH), 3.98 (1H, dd, 4.3, 9.9 Hz, CHOCH2), 4.50 (1H, m, NHCHCH), 4.57 (1H, t, J=4.9 Hz, TsOCHCH), 5.03 (1H, m, TsOCHCH), 5.71 (1H, b, NH), 7.52 (2H, d, J=8.0 Hz, aryl), 7.84 (2H, d, J=8.0 Hz, aryl), 9.92 (2H, b, OH+HCl); δC (125 MHz, d6-DMSO) 21.25 (aryl-CH3), 45.99 (NHCH2), 67.60 (NHCH), 72.63 (OCH2CHOH), 75.94 (OCH2CHOH), 77.18 (TsOCHCH), 79.15 (TsOCHCH), 127.84 and 130.40 (aromatic CH), 132.28 (CHOSO2C quaternary), 145.65 (CH3C quaternary).