Sodium Carbonate → HCID 69103883, 화합물

HRID 2220375노트

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HRID 2220375 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:37]([C:45]3[S:46][CH:47]=[CH:48][CH:49]=3)[CH:36]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.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>[C:13]([O:12][C:11]([N:10]([CH2:18][C@H:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:37]([C:45]3[S:46][CH:47]=[CH:48][CH:49]=3)[CH:36]=2)=[CH:3][CH:4]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 24824073HCID 24824073, 화합물HCID 69103033HCID 69103033, 화합물

생성물 1

HCID 69103883HCID 69103883, 화합물수율 51.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-hydroxy-2-phenylethyl]carbamate (280 mg) in 1,2-dimethoxyethane (4 ml) was added methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2-thienyl)benzoate (275 mg), tetrakis(triphenylphosphine)palladium (62 mg) and aqueous solution of sodium carbonate (2M, 0.7 ml), and the mixture was stirred at 80° C. for 4 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[(tert-butoxycarbonyl) [(2R)-2-hydroxy-2-phenylethyl]amino]-ethyl]-3-(2-thienyl)-4-biphenylcarboxylate (191 mg).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-cc82f06c35f648d292f297e76b07099a
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417060B2

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