Lithium hydroxide, monohydrate → 6-Cyano-7-(4-(3',4'-dimethylbiphenyl-3-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid

HRID 1048073노트

반응식

HRID 1048073 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:36])[NH:21][C:22]3[CH:23]=[C:24]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=4)[CH:25]=[CH:26][CH:27]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:37]([O:39]C)=[O:38])#[N:2].O[Li].O.O1CCOCC1.Cl>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:36])[NH:21][C:22]3[CH:23]=[C:24]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=4)[CH:25]=[CH:26][CH:27]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:37]([OH:39])=[O:38])#[N:2]

참가 물질

5

반응물 3

HCID 168937Lithium hydroxide, monohydrateHCID 204431481,4-Dioxane hydrochlorideHCID 67080482Methyl 6-cyano-7-(4-(3',4'-dimethylbiphenyl-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate

생성물 1

HCID 445999186-Cyano-7-(4-(3',4'-dimethylbiphenyl-3-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid수율 88.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 6-cyano-7-(4-(3′,4′-dimethylbiphenyl-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (36 mg, 0.06759 mmol) was dissolved in THF (2 ml) and 1M solution of LiOH—H2O (135.2 μL, 0.135 mmol) was added. The mixture was stirred for 17 hours at ambient temperature. The mixture was quenched with 4M HCl dioxane (50.70 μL, 0.203 mmol). The crude mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient) to provide 31 mg of the title compound as a thin film (90%). MS (apci) m/z=519.1 (M+H).

후처리

  1. customThe crude mixture was purified on silica gel (MeOH in dichloromethane with 1% acetic acid gradient)

출처 및 근거

ORD 기록
ord-84fc87bca3f1446ea6b8cb510dae7075
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569522B2

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