Trifluoroacetic acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

HRID 1037407노트

반응식

HRID 1037407 반응식
FC(F)(F)C(O)=O.C(OC([NH:15][C:16]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([C:37]([OH:39])=[O:38])[CH:31]=[CH:32][CH:33]=4)[O:28][C:27]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17]1)=O)(C)(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:15][C:16]1([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([C:37]([OH:39])=[O:38])[CH:31]=[CH:32][CH:33]=4)[O:28][C:27]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:24][CH:25]=2)[CH2:17][CH2:18][CH2:19]1

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acid2회HCID 670678653-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

생성물 1

HCID 670679903-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid수율 69.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

trifluoro-acetic acid: 3-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid (18 mg, 0.035 mmol) was treated with a solution of 25% TFA in DCM (4 mL) and stirred at RT for 1 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The resultant residue was triturated with diethyl ether and DCM, and concentrated in vacuo to give the title compound as a light tan solid (10 mg, 54%). 1H NMR (400 MHz, DMSO-d6): δ 13.44 (bs, 1H), 8.44 (s, 3H), 8.28-8.23 (m, 2H), 7.57 (t, J=7.7 Hz, 1H), 7.48-7.36 (m, 5H), 7.33-7.27 (m, 4H), 2.64-2.53 (m, 2H), 2.51-2.42 (m, 2H), 2.18-2.05 (m, 1H), 1.85-1.73 (m, 1H). LCMS (Method E): RT=2.89 min, [M+H]+=412.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was triturated with diethyl ether and DCM
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3130de00525c43d3b35e2a12ea873bf4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

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