Triphenylphosphine → HCID 67453620, compound

HRID 1713270Notes

Reaction equation

HRID 1713270 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:23]([O:30][CH2:31][CH2:32][CH2:33][CH2:34]O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.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>O1CCCC1>[CH2:23]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5622124-Benzyloxy-1-butanolHCID 67456175HCID 67456175, compound

Product 1

HCID 67453620HCID 67453620, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-(3′-hydroxybiphenyl-4-ylmethyl)carbamate (0.400 g), 4-benzyloxy-1-butanol (0.313 g) and triphenylphosphine (0.456 g) in tetrahydrofuran (6.7 mL) was added dropwise diisopropyl azodicarboxylate (40% toluene solution, 0.878 g), and the resulting mixture was stirred at room temperature for 75 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/ethyl acetate=6/1) to give the title compound (0.551 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-3cbe2b6ee5a148cda9b874e66fbfd9ae
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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