Sulfuric Acid → HCID 68996119, compound

HRID 1909686Notes

Reaction equation

S1(=O)(=O)[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C@H:4]2[CH2:3][O:2]1.[Cl:12][C:13]1[CH:26]=[CH:25][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].OS(O)(=O)=O.[OH-].[Na+]>CN(C=O)C>[ClH:12].[Cl:12][C:13]1[CH:26]=[CH:25][C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:2][CH2:3][C@@H:4]3[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]3)=[CH:20][CH:19]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of (S)-hexahydro-[1,2,3]oxathiazolo[3,4-a]pyridine 1,1-dioxide (83 mg, 0.47 mmol), 4-(4-chloro-phenoxy)-phenol (80 mg, 0.36 mmol), and potassium carbonate (99 mg, 0.72 mmol) in DMF (2.5 mL) was heated for 18 h at 65° C. The ambient mixture's pH was adjusted to 1 with an aqueous 20% H2SO4 solution and stirred at ambient temperature for about 20 h. The reaction solution's pH was adjusted to 12-14 with 5N NaOH, and extracted with EtOAc (2×18 mL). The organic layers were combined, dried over anhydrous Na2SO4, and concentrated to an oil. The oil was treated with 2M HCl in ether to give the desired product as a white solid (22 mg, 13%): MS; m/z 318 (MH)+; LCMS (UV) 99% HPLC 99.5%; 1H NMR (400 MHz, DMSO-d6) δ 1.50-1.88 (m, 6H), 2.90-2.97 (m, 1H), 3.25 (d, 1H, J=12.8 Hz), 3.42-3.47 (m, 1H), 4.09-4.13 (dd, 1H J1=7.2 Hz, J2=10.4 Hz), 4.17-4.21 (dd, 1H J1=4 Hz, J2=10.8 Hz)), 6.93-6.96 (m, 2H), 7.06-7.08 (m, 4H); 7.39-7.41 (m, 2H) 9.155 (s, 2H)

Workup

extractionextracted with EtOAc (2×18 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated to an oil
additionThe oil was treated with 2M HCl in ether

Sources & evidence

ORD record: ord-47fe976df71d4ea483f5c8bd0bdd0bd7
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598359B2

Reaction notes

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