Triphenylphosphine → HCID 69420852, compound

HRID 456466Notes

Reaction equation

HRID 456466 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][CH2:11][CH:12](C)CO)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[OH:36])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].[C:37]1(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:17]([O:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[O:36][CH2:37][CH:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:16])[CH3:12])[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylateHCID 53397682HCID 53397682, compound

Product 1

HCID 69420852HCID 69420852, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3-Hydroxy-2-methyl-propyl)-carbamic acid benzyl ester (5.0 g, 24.0 mmol) was dissolved in THF (175 mL) at 0° C. 4-(2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (6.7 g, 24.0 mmol) and triphenylphosphine (7.6 g, 29.0 mmol) were added. Diisopropyl azodicarboxylate (5.75 mL, 29.0 mmol) was added dropwise, and the mixture was stirred overnight. The mixture was concentrated under reduced pressure and purified using silica gel chromatography (25% ethyl acetate in hexanes) to afford the title compound (5.33 g, 47%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified

Sources & evidence

ORD record
ord-a14c117b2d5448e68f3ebaa49c3e50fd
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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