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Potassium Carbonate → 2-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid methyl ester

HRID 900378
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HRID 900378 반응식
[CH3:1][O:2][C:3](=[O:22])[CH:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1.[CH:23]1[C:31]2[C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[O:28][C:27]=2[C:26]([C:36]2[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=2)=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:22])[CH:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:39]2[CH:40]=[CH:41][C:36]([C:26]3[C:27]4[O:28][C:29]5[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=5[C:31]=4[CH:23]=[CH:24][CH:25]=3)=[CH:37][CH:38]=2)=[CH:9][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 59655966(4-(Dibenzo[b,d]furan-4-yl)phenyl)boronic acidHCID 596962102-tert-Butoxycarbonylamino-3-(4-bromophenylsulfanyl)-propanoic acid methyl ester

생성물 1

HCID 1317268282-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid methyl ester수율 72%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-tert-Butoxycarbonylamino-3-(4-bromophenylsulfanyl)-propanoic acid methyl ester (0.55 g, 1.41 mmol), 4-(4-dibenzofuranyl)benzeneboronic acid (0.44 g, 1.52 mmol) and Pd(PPh3)4 (0.073 g, 5 mol %) in toluene (15 mL) and ethanol (3.0 mL) was treated with 2 M K2CO3 (2.2 mL). The reaction mixture was heated to reflux for 2 h, cooled to room temperature, diluted with ethyl acetate (100 mL). The organic layer was washed successively with 2% aq HCl and sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (2-10% ethyl acetate in heptane) gave the desired product (552 mg, 72%) as a white solid. 1H NMR (CDCl3), δ 8.01 (d, J=6 Hz, 2H), 7.96 (dd, J=4 Hz, 8 Hz, 2H), 7.74 (d, J=9 Hz, 2H), 7.66 (m, 4H), 7.42 (m, 5H), 5.41 (d, J=7 Hz, 1H), 4.62 (m, 1H), 3.73 (s, 3H), 3.45 (d, J=4 Hz, 2H), 1.57 (s, 9H). LCMS 454 (M+−100).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. washThe organic layer was washed successively with 2% aq HCl and sat. aq NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (2-10% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-01df2e154bd241688143bf39228b0280
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07358248B2

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