Hydrochloric Acid → HCID 10272938, compound

HRID 2415211Notes

Reaction equation

C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[CH:12]([C:18]2[CH:27]=[C:26]3[C:21]([C:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25]3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH3:28][C:22]1([CH3:29])[C:21]2[C:26](=[CH:27][C:18]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=3)=[O:30])=[CH:19][CH:20]=2)[O:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptanoylamino]-benzoic acid methyl ester (0.15 g, 0.35 mmole) in 10 mL of a 4:1 THF/methanol mixture was treated with a solution of 0.1 g of lithium hydroxide monohydrate in 2.5 mL of water and stirred at 40° C. for 6 hours. The mixture was diluted with 10 mL of water and the pH adjusted to 2.0 with 2N HCl solution. The mixture was extracted with three 10 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 10% methanol in dichloromethane) to yield 0.11 g of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptanoylamino]-benzoic acid as a white powder. MS (ESI): (M−): 408.

Workup

extractionThe mixture was extracted with three 10 mL portions of ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a yellow oil
customThe product was purified by flash chromatography (SiO2, 10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-fe9afa48c20849f2b7e1ac12e7a87ba5
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818652B2

Reaction notes

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