Water → 1,1-Dimethylethyl N-((6-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 1868806노트

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HRID 1868806 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:5]2[OH:26].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+].O>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:27]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[O:16])=[C:5]3[OH:26])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

9

반응물 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67099310HCID 67099310, 화합물

생성물 1

HCID 670999281,1-Dimethylethyl N-((6-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate수율 68.5%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

To 1,1-dimethylethyl N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (250 mg, 658 μmol, Example 40A-D), phenylboronic acid (120 mg, 987 μmol), Pd2(dba)3 (60.3 mg, 65.8 μmol), and X-Phos (62.8 mg, 132 μmol), were added dioxane (3291 μL) and K2CO3 in water (987 μL, 1975 μmol). The reaction was then heated at 110° C. for 6 hours. The resulting reaction mixture was cooled to ambient temperature, diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (190 mg) as an amber amorphous solid after purification via prep-LC. MS (m/z)=444(M+Na)+.

후처리

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to ambient temperature
  3. additionadded to a separatory funnel
  4. custompartitioned with NaHCO3 (saturated, aqueous)
  5. washwashed 2 times with 50 mL of NaHCO3 (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fd8f4f255a7644fc95d44080c199a937
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635715B2

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