Triphenylphosphine → Methyl 2-{4-[(tert-butoxycarbonyl)amino]butoxy}-6-hydroxybenzoate

HRID 488657

반응식

HRID 488657 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[OH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20](O)[C:16]=1[C:17]([O-:19])=[O:18].[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[C:9]([O:8][C:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:20]1[CH:21]=[CH:22][CH:23]=[C:15]([OH:14])[C:16]=1[C:17]([O:19][CH3:25])=[O:18])=[O:13])([CH3:10])([CH3:12])[CH3:11]

참가 물질

5

반응물 4

HCID 11776TriphenylphosphineHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 178524827HCID 178524827, 화합물

생성물 1

HCID 10980693Methyl 2-{4-[(tert-butoxycarbonyl)amino]butoxy}-6-hydroxybenzoate

실험 절차

To a round bottom flask was charged with tert-butyl 4-hydroxybutylcarbamate (400 mg, 2.1 mmol), 463 mg of 2,6-dihydroxybenzoate (463 mg, 2.7 mmol), and triphenylphosphine (777 mg, 3.0 mmol). The flask was vacuumed and back flushed with nitrogen (3×), capped with a rubber septum, and kept under positive nitrogen atmosphere. THF (anhydrous) was then added, followed by dropwise addition of DEAD (433 μL, 2.7 mmol). Most of the starting material was consumed within the first 30 min. Solvent was then removed in vacuo, and the residue was purified on a silica gel chromatography eluting with 15-30% EtOAc in hexane to give the ether product (410 mg, 57%) as a cloroless oil.

후처리

  1. customback flushed with nitrogen (3×)
  2. customcapped with a rubber septum
  3. additionTHF (anhydrous) was then added
  4. customMost of the starting material was consumed within the first 30 min
  5. customSolvent was then removed in vacuo
  6. customthe residue was purified on a silica gel chromatography
  7. washeluting with 15-30% EtOAc in hexane
  8. customto give the ether product (410 mg, 57%) as a cloroless oil

출처 및 근거

ORD 기록
ord-34878e310ca74234ace5aadad2a82f99
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972340B2

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