Tetrahydrofuran → HCID 46916262, compound

HRID 1616694Notes

Reaction equation

[NH2:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[C:20]([NH:1][C:2](=[S:10])[NH:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=[O:21])[C:19]1[CH:18]=[CH:22][CH:11]=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 8028Tetrahydrofuran

HCID 11543400HCID 11543400, compound

Product 1

HCID 46916262HCID 46916262, compoundYield 80%

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.099 g, 0.39 mmol, 1 equiv.) and PhCONCS (0.06 mL, 0.4 mmol, 1 equiv.) were dissolved in THF (2 mL) and stirred at 50° C. for 16 h. The solvent was removed and the product was purified by preparatory HPLC (0-30% EtOAC:hexanes). The product was isolated as a white solid (0.131 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ 14.75 (s, 1H), 9.21 (s, 1H), 7.92 (dd, J=5.2, 3.3 Hz, 2H), 7.64-7.57 (m, 1H), 7.54-7.46 (m, 2H), 4.71 (s, 2H), 3.94 (t, J=5.6 Hz, 2H), 2.90 (t, J=5.6 Hz, 2H), 1.63 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 173.72, 165.23, 164.54, 147.15, 133.48, 131.81, 129.36, 129.04, 127.77, 125.77, 117.76, 82.36, 65.20, 64.71, 28.51, 27.38.

Workup

customThe solvent was removed
customthe product was purified by preparatory HPLC (0-30% EtOAC:hexanes)

Sources & evidence

ORD record: ord-e5a5f9e6c96c456a8a6be380097bc6bb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765803B1

Reaction notes

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