HCID 57857023, compound → HCID 44206775, compound

HRID 561755Notes

Reaction equation

HRID 561755 reaction equation
[S:1]1[C:5]([C@H:6]([O:31]C2CCCCO2)/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([O:14]C3CCCCO3)[CH2:12][C:11](=[O:21])[C@@H:10]2[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:4][C:3]2[CH:38]=[CH:39][CH:40]=[CH:41][C:2]1=2>C(O)(=O)C.O.C1COCC1>[S:1]1[C:5]([C@H:6]([OH:31])/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([OH:14])[CH2:12][C:11](=[O:21])[C@@H:10]2[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:4][C:3]2[CH:38]=[CH:39][CH:40]=[CH:41][C:2]1=2

Participants

3

Reactant 1

HCID 57857023HCID 57857023, compound

Product 1

HCID 44206775HCID 44206775, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

(Z)-7-((1R,2R,3R)-2-((3R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tetrahydro-2H-pyran-2-yloxy)prop-1-enyl)-5-oxo-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (33) was dissolved in a 4:2:1 solution of acetic acid-water-THF (0.5 M). The solution was stirred for several days at room temperature until the reaction was complete, as judged by TLC. The crude product was purified by flash chromatography on regular silica gel using ethyl acetate-hexane-0.5% acetic acid as eluent to afford the title compound 14a; TLC: Rf=0.20 (silica on 10 mm aluminum plates, eluent: 40:60:1 hexanes-ethyl acetate-acetic acid); MS (−cESI) m/z 413 (M−1); LC/MS: Sample prep-diluent, methanol. Sample prepared in 100 μL, unknown final concentration, analytical method: column: Phenomenex Synergi Hydro-RP 4p 250×2.00 mm, flow rate 0.2 mL/min, detection UV (210 nm), column temperature 25° C., HPLC mobile phase: isocratic mobile phase consisting of 31.3% solvent A, 68.7% solvent B, Solvent A=10:90:0.1 methanol-water-acetic acid, Solvent B=90:10:0.1 methanol-water-acetic acid.

Workup

  1. customThe crude product was purified by flash chromatography on regular silica gel

Sources & evidence

ORD record
ord-26d982d0966e40ef84e726b0997b4597
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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