Methanol → 7-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyano-4-methylchroman-4-carboxylic acid

HRID 510597노트

반응식

HRID 510597 반응식
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:34]=[CH:33][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([C:20]([CH3:30])([C:26]([O:28]C)=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:31]#[N:32])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].O.CO>C1COCC1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([C:20]([CH3:30])([C:26]([OH:28])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:31]#[N:32])=[CH:33][CH:34]=2)=[O:10])=[CH:35][CH:36]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67080322Methyl 7-(4-((4-chlorophenethyl)carbamoyl) phenoxy)-6-cyano-4-methylchroman-4-carboxylate

생성물 1

HCID 670804267-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyano-4-methylchroman-4-carboxylic acid수율 34.3%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyano-4-methylchroman-4-carboxylate (12 mg, 0.0238 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (0.0475 mL, 0.238 mmol) and 200 μL of water and methanol. After stirring for 3 hours, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using the Horizon with a 25 cartridge and running a gradient 0.5% methanol/0.5% acetic acid/CH2Cl2 to 10% methanol/0.5% acetic acid/CH2Cl2 to yield the title compound (4.0 mg, 34.3% yield) as a white solid. MS (ESI)=490.9 (M+1).

후처리

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified

출처 및 근거

ORD 기록
ord-783d4c62ffcf4399a2b0dae07ae7b57d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096567B2

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