5-Cyclopentyl-5-hydroxy-9-(4-hydroxy-2,5-dimethyl-phenyl)-3-oxo-non-8-ynoic Acid Methyl Ester → 3-[4-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-but-1-ynyl]-benzenesulfonamide

HRID 1453319Notes

Reaction equation

HRID 1453319 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5](=[O:28])[CH2:6][C:7]([CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)([OH:22])[CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18](=[O:21])(=[O:20])[NH2:19])[CH:13]=1.COC(=O)CC(=O)CC(C1CCCC1)(O)CCC#CC1C=C(C)C(O)=CC=1C>>[CH:23]1([C:7]2([CH2:8][CH2:9][C:10]#[C:11][C:12]3[CH:13]=[C:14]([S:18]([NH2:19])(=[O:20])=[O:21])[CH:15]=[CH:16][CH:17]=3)[CH2:6][C:5](=[O:28])[CH2:4][C:3](=[O:2])[O:22]2)[CH2:24][CH2:25][CH2:26][CH2:27]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 587625735-Cyclopentyl-5-hydroxy-3-oxo-9-(3-sulfamoyl-phenyl)-non-8-ynoic acid methyl ester

Product 1

HCID 587625983-[4-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-but-1-ynyl]-benzenesulfonamide

Procedure

The desired product was prepared analogously to example F(1), substituting 5-cyclopentyl-5-hydroxy-3-oxo-9-(3-sulfamoyl-phenyl)-non-8-ynoic acid methyl ester (80 mg, 0.19 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: 17 mg, 23%. 1H NMR (CDCl3) δ: 1.43-1.74 (m, 8H), 1.93-2.05 (m, 2H), 2.20 (p, J=8.59 Hz, 1H), 2.52 (t, J=7.45 Hz, 2H), 2.70 (d, J=16.17 Hz, 1H), 2.80 (d, J=16.17 Hz, 1H), 3.39 (s, 2H), 4.82 (s, 2H), 7.38 (t, J=7.83 Hz, 1H), 7.50 (d, J=8.84 Hz, 1H), 7.76 (d, J=7.83 Hz, 1H), 7.90 (t, J=1.52 Hz, 1H). MS (ESI): 388 (M−H).

Sources & evidence

ORD record
ord-a7938ffa644a4561a01d2f27eaf71930
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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