Water → HCID 68750593, compound

HRID 573528Notes

Reaction equation

C1COCC1.O.[OH:7][C@@H:8]([CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:20]2[C@@H:14]([O:15][CH2:16][C@@H:17]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:19]2)[CH2:13][C@H:12]1[O:30]C1CCCCO1>C(O)(=O)C>[OH:30][C@@H:12]1[CH2:13][C@@H:14]2[O:15][CH2:16][C@@H:17]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:19][C@@H:20]2[C@H:11]1/[CH:10]=[CH:9]/[C@@H:8]([OH:7])[CH2:37][O:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 60 °C

Procedure

THF (400 μL) and water (400 μL) were added to an acetic acid solution (800 μL) of the compound (151 mg, 0.259 mmol) produced in Example 15, followed by stirring at 60° C. for 3 hours and 30 minutes. The reaction solution was concentrated under reduced pressure, and purified with a column apparatus (Hiflash-SI, Size S, ethyl acetate:hexane=1:1→ethyl acetate) manufactured by Yamazen Corporation to obtain a titled compound (74 mg) having the following physical property values. TLC: Rf 0.28 (dichloromethane:methanol=20:1); 1H-NMR (300 MHz, CDCl3): δ 0.90-1.19, 1.22, 1.36-1.83, 1.84-1.96, 2.03-2.18, 2.23, 2.41-2.53, 2.57, 2.84-2.97, 3.64-3.80, 3.83-3.91, 3.92-4.09, 4.44-4.59, 4.88-5.09, 5.53-5.77, 6.83-7.04, 7.14-7.35.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
custompurified with a column apparatus (Hiflash-SI, Size S, ethyl acetate:hexane=1:1→ethyl acetate)

Sources & evidence

ORD record: ord-f4a1f5f4afdd495ead178f235e473cd3
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029574B2

Reaction notes

Loading…