Hydrochloric Acid → HCID 21018228, compound

HRID 1744220Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([O:21]COC)[CH2:11][C@@H:10]4[CH3:25])[CH2:7][CH2:6][C:5]=2[CH:4]=1.Cl.C([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][C@@H:10]4[CH3:25])[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 9 mg (0.026 mmol) of 59, 5 μL of concentrated HCl, in MeOH (2 mL) was stirred at rt for 15 min then heated at 60° C. for 30 min. Another 25 mL of concentrated HCl was added and the reaction was stirred at 60° C. for 1 h. The reaction mixture was poured into saturated aqueous NaHCO3 (5 mL) and extracted with EtOAc (3×, 5 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo giving a clear yellow oil. Purification by flash chromatography on 2×17 cm column of silica gel using 2:1 hexanes/EtOAc as eluent gave 7.3 mg (93%) of 6025. Data for 60: TLC, T-1, Rf 0.31; 1H NMR (400 MHz, CDCl3) δ 0.82 (s, 3H, H-18), 0.90 (t, 1H, J=10.2 Hz, H-14) 1.13 (d, 3H, J=6.3 Hz, 15α-CH3), 3.76 (t, 1H, J=8.7 Hz, H-17α), 3.79 (s, 3H, ArOCH3), 6.63 (d, 1H, J=2.7 Hz, H-4), 6.72 (dd, 1H, J=8.6, 2.7 Hz, H-2), 7.22 (d, 1H, J=8.6 Hz, H-1).

Workup

extractionextracted with EtOAc (3×, 5 mL)
dry with materialCombined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customgiving a clear yellow oil
customPurification by flash chromatography on 2×17 cm column of silica gel using 2:1 hexanes/EtOAc as eluent

Sources & evidence

ORD record: ord-5ee3d26d5d254cf1a31d9aa9c2eb968f
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07015211B2

Reaction notes

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