Hydrochloric Acid → HCID 10525398, compound

HRID 1016268Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([O:27]C(=O)C)[C@H:17]([C:31]([OH:33])=[O:32])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O.Cl>CO>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:27])[C@H:17]([C:31]([OH:33])=[O:32])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 784.4 mg (1.75 mmol) of 6, 5% aqueous KOH in MeOH (7 mL) was stirred and heated at 50° C. for 3 h. Reaction was cooled to rt, poured into H2O (50 mL), adjusted to pH 1 with 10% aqueous HCl, and extracted with EtOAc (3×, 100 mL). Combined organic extracts were washed with H2O (100 mL), dried over Na2SO4, and concentrated in vacuo. Purification of the residue by flash chromatography on a 2×17 cm column of silica gel using EtOH/EtOAc (10:90) gave 491.5 mg (69%) of 7 as a white foam. Data for 7: TLC, T-4, Rf0.63. 1H NMR (500 MHz, CDCl3) δ 0.86 (2, 3H, H-18), 3.94 (d, 1H, J=8.3 Hz, H-17α), 5.04 (s, 2H, benzylic), 6.73 (d, 1H, J=2.2 Hz, H-4), 6.80 (dd, 1H, J=8.7, 2.2 Hz, H-2), 7.21 (d, 1H, J=8.7 Hz, H-1), 7.32-7.45 (m, 5H, Ar—H).

Workup

customReaction
temperaturewas cooled to rt
extractionextracted with EtOAc (3×, 100 mL)
washCombined organic extracts were washed with H2O (100 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customPurification of the residue by flash chromatography on a 2×17 cm column of silica gel

Sources & evidence

ORD record: ord-4f19d226a0bc4bde90a5385c400252dc
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476012B2

Reaction notes

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