Hydrochloric Acid → HCID 9840634, compound

HRID 1354814Notes

Reaction equation

[OH-].[Na+].C([O:10][C:11](=[O:34])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][C:13]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1.Cl>CO>[CH2:27]([O:26][C:13]1[CH:14]=[C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:17][C:12]=1[C:11]([OH:34])=[O:10])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 65 °C

Procedure

NaOH (1 N) (150 mL) was added to compound 36 (4.3 g) in MeOH (50 mL). The reaction mixture was heated to 65° C. with stirring for 48 h. After the reaction mixture was cooled down to room temperature, 1.0 M HCl (200 mL) was added to neutralize the reaction mixture. The solvent was concentrated under reduced pressure. The residue was extracted with CHCl3 and H2O. The combined organic layer was dried over MgSO4. After the MgSO4 was filtered off, the solvent was removed under reduced pressure. The residue was purified by flash chromatography to give the compound 37 (1.3 g) as a solid with total yield of 38.92% for 2 steps. LC-MS (ESI): m/e=335.2 [M+1]+

Workup

temperatureAfter the reaction mixture was cooled down to room temperature
concentrationThe solvent was concentrated under reduced pressure
extractionThe residue was extracted with CHCl3 and H2O
dry with materialThe combined organic layer was dried over MgSO4
filtrationAfter the MgSO4 was filtered off
customthe solvent was removed under reduced pressure
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-385dc4a5f9c64d6d9acfe15963fdfeec
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223759B2

Reaction notes

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