Triphenylphosphine → HCID 69850004, compound

HRID 1459397Notes

Reaction equation

HRID 1459397 reaction equation
[C:1]12([NH:11][C:12](=[O:31])[C:13]([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH2:14][CH2:15]O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]12([N:11]3[CH2:15][CH2:14][C:13]([CH2:17][C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)([CH2:24][C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[C:12]3=[O:31])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57250797HCID 57250797, compound

Product 1

HCID 69850004HCID 69850004, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2 atmosphere were combined N-adamantan-1-yl-4-hydroxy-2,2-bis-pyridin4-ylmethyl-butyramide (50 mg, 0.24 mmol), triphenylphosphine (63 mg, 0.24 mmol), and diisopropylazodicarboxylate (0.047 ml, 0.24 mmol) in 5 ml THF and the resulting solution was allowed to stir for 18 hours. The reaction mixture was then placed directly on a silica gel column and eluted with 85:15 mix of EtOAc/MeOH to yield 46 mg of product as a gum which in turn could be crystallized from isopropylether/hexane to yield the desired product as a white solid, m.p. 163.5°-165° C.

Workup

  1. washeluted with 85:15
  2. additionmix of EtOAc/MeOH

Sources & evidence

ORD record
ord-412a0a508bc540bd9bd3aaa3fbe35af9
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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