Water → HCID 68750593, compound

HRID 1915208Notes

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-6e2c6bc7010c495f9e636f6629dc70c1
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614340B2

Reaction notes

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