Benzyl Alcohol → HCID 69156334, compound

HRID 750209Notes

Reaction equation

HRID 750209 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[C:20](C(O)=O)=[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([Br:30])[CH:17]=4)[C:12]3=[O:31])=[CH:9][C:4]=2[O:3][CH2:2]1.C([N:34]([CH2:37]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[CH2:56]([OH:63])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C1(C)C=CC=CC=1>[CH2:56]([O:63][C:37](=[O:46])[NH:34][C:20]1[N:11]([CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)[C:12](=[O:31])[C:13]2[C:18]([C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:17][C:16]([Br:30])=[CH:15][CH:14]=2)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23060580HCID 23060580, compound

Product 1

HCID 69156334HCID 69156334, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (220 mg), triethylamine (91 μl) and toluene (4.4 ml) was added diphenylphosphorylazide (185 μl) at room temperature with stirring, and the mixture was stirred at room temperature for 1 hr. and at 80° C. for 1 hr. After cooling, benzyl alcohol (79 μl) was added to the reaction mixture, and the mixture was further stirred at 80° C. for 12 hrs. After cooling the reaction mixture, the solvent was evaporated under reduced pressure and the residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1) to give the title compound (160 mg) as pale-yellow crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. temperatureAfter cooling
  3. stirringthe mixture was further stirred at 80° C. for 12 hrs
  4. temperatureAfter cooling the reaction mixture
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=4/1-1/1)

Sources & evidence

ORD record
ord-c52f1d831b4146a4966ca0fa68abb7e6
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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