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

HRID 488657

反応式

HRID 488657 の反応式
[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]

参加物

5

反応物 4

HCID 11776TriphenylphosphineHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 178524827HCID 178524827、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-34878e310ca74234ace5aadad2a82f99
出典データセット
uspto-grants-2005_12
特許番号
US06972340B2

関連ノート

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