5-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl Ester → 6-Cyclopentyl-6-[4-(2-methylsulfanyl-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

HRID 1453320Notes

Reaction equation

HRID 1453320 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5](=[O:26])[CH2:6][C:7]([CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)(O)[CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18][CH3:19].COC(=O)CC(=O)CC(C1CCCC1)(O)CCC#CC1C=C(C)C(O)=CC=1C>>[CH:21]1([C:7]2([CH2:8][CH2:9][C:10]#[C:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18][CH3:19])[O:27][C:3](=[O:2])[CH2:4][C:5](=[O:26])[CH2:6]2)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 587623975-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl EsterHCID 587627625-Cyclopentyl-5-hydroxy-9-(2-methylsulfanyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester

Product 1

HCID 587624926-Cyclopentyl-6-[4-(2-methylsulfanyl-phenyl)-but-3-ynyl]-dihydro-pyran-2,4-dione

Procedure

The desired product was prepared analogously to example F(1), substituting 5-cyclopentyl-5-hydroxy-9-(2-methylsulfanyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester (43 mg, 0.11 mmol) from Step 2 below in place of 5-cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic acid methyl ester. Yield: 38 mg, 97%. 1H NMR (CDCl3) δ: 1.41-1.69 (m, 8H), 1.94-2.01 (m, 2H), 2.13-2.18 (m, 1H), 2.36 (s, 3H), 2.55 (t, J=7.45 Hz, 2H), 2.67 (d, J=16.17 Hz, 1H), 2.87 (d, J=16.17 Hz, 1H), 3.34 (d, J=8.84 Hz, 2H), 6.93-7.01 (m, 2H), 7.14-7.16 (m, 1H), 7.24 (d, J=6.32 Hz, 1H). MS (ESI): 355 (M−H).

Sources & evidence

ORD record
ord-97f039af9ef04e70bfbc460125f23bd2
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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