N-Hydroxyphthalimide → Di-tert-butyl [{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidin-1-yl}methylylidene]biscarbamate

HRID 2400636노트

반응식

HRID 2400636 반응식
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[C:13]([O:17][C:18](=[O:36])[NH:19][C:20]([N:29]1[CH2:34][CH2:33][CH:32](O)[CH2:31][CH2:30]1)=[N:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:24]([O:23][C:22](=[O:28])[NH:21][C:20]([N:29]1[CH2:34][CH2:33][CH:32]([O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:31][CH2:30]1)=[N:19][C:18](=[O:36])[O:17][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:25])([CH3:26])[CH3:27]

참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67271828[Tert-butoxycarbonylimino-(4-hydroxy-piperidin-1-yl)-methyl]-carbamic acid tert-butyl ester

생성물 1

HCID 86699594Di-tert-butyl [{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidin-1-yl}methylylidene]biscarbamate수율 31.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of N-hydroxyphthalimide (1.89 g, 11.62 mmol), di-tert-butyl[(4-hydroxypiperidin-1-yl)methylylidene]biscarbamate 63 (2.00 g, 5.81 mmol, US 2004/209921 A1) and triphenylphosphine (3.05 g, 11.62 mmol) in THF (100 mL) was added diisopropyl azodicarboxylate (2.47 mL, 12.78 mmol) slowly at room temperature. The resulting mixture was stirred at room temperature overnight and concentrated to provide a residue which was subjected to chromatography to give 64 (0.9 g) as a white solid.

후처리

  1. concentrationconcentrated
  2. customto provide a residue which

출처 및 근거

ORD 기록
ord-aa734fadc28a4030a418e51e11f3c2ca
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796257B2

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