Methanol → HCID 10582652, compound

HRID 1016271Notes

Reaction equation

HRID 1016271 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]([OH:27])[C@H:17]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[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.[CH3:33]O>>[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]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[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

3

Reactant 2

HCID 887MethanolHCID 10670484HCID 10670484, compound

Product 1

HCID 10582652HCID 10582652, compound

Procedure

Compound 33 was prepared by esterification of crude 32 (436 mg) with MeOH as described for the preparation of 9. Purification of the residue by flash chromatography on a 3×21 cm column of silica gel using hexanes/EtOAc (2:1) as eluent gave 268 mg (52%, three steps) 33 as a white solid. Data for 33: TLC, T-5, Rf0.76. 1H NMR (500 MHz, CDCl3) δ 0.81 (s, 3H, H-1 8), 2.84 (m, 2H, H-6), 3.31 (d, 1H, J=7.3 Hz, H-17α), 3.69 (s, 3H, OCH3), 5.04 (s, 2H, benzylic), 6.72 (d, 1H, J=2.8 Hz, H-4), 6.79 (dd, 1H, J=8.6, 2.8 Hz, H-2), 7.21 (d, 1H, J=8.6 Hz, H-1), 7.31-7.44 (m, 5H, Ar—H); HRMS (ES) calcd for C29H36O4Na (M+Na+) m/e 471.2511, found m/e 471.2513.

Workup

  1. customas described for the preparation of 9
  2. customPurification of the residue by flash chromatography on a 3×21 cm column of silica gel

Sources & evidence

ORD record
ord-5a8c7281c2174677b1bd415be10a3b7c
Source dataset
uspto-grants-2002_11
Patent number
US06476012B2

Reaction notes

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