Acetonitrile → HCID 87416434, compound

HRID 2273036Notes

Reaction equation

HRID 2273036 reaction equation
[NH2:1][CH:2]1[CH:17]([OH:18])[CH:6]2[O:7][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][CH2:10][CH:5]2[CH2:4][CH:3]1[OH:19].[CH2:20]([S:22]N=C=O)C.[C:26](#[N:28])[CH3:27]>>[OH:19][C@H:3]1[C@H:2]([NH:1][C:20]([NH:28][CH2:26][CH3:27])=[S:22])[C@@H:17]([OH:18])[C@@H:6]2[O:7][C@H:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:9][CH2:10][C@H:5]2[CH2:4]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 21933416HCID 21933416, compoundHCID 67481674HCID 67481674, compound

Product 1

HCID 87416434HCID 87416434, compoundYield 100%

Conditions

Temperature
60 °C

Procedure

To a suspension of the amine from above (85 mg, 0.32 mmol) in acetonitrile (3 mL) was added ethylthioisocyanate (34 mg, 0.39 mmol). The mixture was heated at 60° C. for 20 h. Solvent was evaporated to give the crude product. This was purified by silica gel chromatography, eluted with EtOAc to give pure rac-1-((2R,4aR,6R,7S,8R,8aR)-6,8-dihydroxy-2-phenylhexahydro-4H-benzo[d][1,3]dioxin-7-yl)-3-ethylthiourea (113 mg, 100%) as a white solid. 1H NMR (600 MHz, CD3OD) δ 7.52-7.50 (m, 2H), 7.40-7.31 (m, 3H), 5.60 (s, 1H), 4.15 (dd, J=10.8, 4.5, 1H), 3.69 (t, J=10.8, 1H), 3.65-3.51 (m, 5H), 1.81 (m, 2H), 1.23 (q, J=12.0, 1H), 1.20 (t, J=7.2, 1H). 13C NMR (151 MHz, CD3OD) 139.85, 129.81, 129.02, 129.03, 127.52, 102.90, 84.75, 75.14, 72.38, 71.88, 65.30, 35.21, 33.19, 14.64.

Workup

  1. customSolvent was evaporated
  2. customto give the crude product
  3. customThis was purified by silica gel chromatography
  4. washeluted with EtOAc

Sources & evidence

ORD record
ord-93df218f6b7340eda9cced3e75f77176
Source dataset
uspto-grants-2015_09
Patent number
US09120781B2

Reaction notes

Loading…