Water → HCID 68750593, compound

HRID 1855676Notes

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, and the mixture was stirred 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);

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-b6672d3073e24e7fa0757ec40541b594
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962868B2

Reaction notes

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