Hydrochloric Acid → 3-{4-[1-Allyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid

HRID 658296노트

반응식

HRID 658296 반응식
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH2:36][CH:37]=[CH2:38])([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]=[CH2:17])=[CH:10][CH:9]=1.[Li+].[OH-].Cl>C1COCC1>[CH2:15]([C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:40])=[O:2])=[O:39])=[CH:13][CH:12]=1)([CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1)[CH2:36][CH:37]=[CH2:38])[CH:16]=[CH2:17]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 674857653-{4-[1-Allyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester

생성물 1

HCID 247653403-{4-[1-Allyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid수율 69.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-{4-[1-allyl-1-(4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester (0.0279 g, 0.0506 mmol) in THF (1.0 mL) is treated with 1N LiOH (1.0 mL) and stirred overnight at room temperature. The reaction mixture is acidified with 1N HCl (2.2 mL) and extracted with EtOAc (3×10 mL). Combined extracts are dried over MgSO4, filtered, and concentrated to provide 3-{4-[1-allyl-1-(4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid (0.0189 g, 69%) as a white solid. MS (ES): 538.3 [M+H]+.

후처리

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialCombined extracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9f991717f7ca4097908e6faa0381d1a0
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076374B2

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