Triphenylphosphine → HCID 68313150, compound

HRID 1530526Notes

Reaction equation

HRID 1530526 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH2:24]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([CH:40](O)[CH3:41])[CH2:36][CH2:35]1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH2:24]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([CH:40]([O:23][C:21]2[CH:20]=[CH:19][C:16]3[C:17]4[N:11]([CH2:12][CH2:13][O:14][C:15]=3[CH:22]=2)[CH:10]=[C:9]([C:8]2[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][N:7]=2)[N:18]=4)[CH3:41])[CH2:36][CH2:35]1)=[O:33])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 18918437Phenylmethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylateHCID 1360309202-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-ol

Product 1

HCID 68313150HCID 68313150, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol (250 mg, 0.80 mmol), 4-(1-hydroxyethyl)piperidine-1-carboxylic acid benzyl ester (233 mg, 0.88 mmol) and PPh3 (316 mg, 1.20 mmol) in dioxane (5 mL) was added DIAD (237 μL, 1.20 mmol) and the resulting yellow solution stirred at RT for 1 h. The reaction mixture was concentrated in vacuo and purified by column chromatography (Si-PCC, gradient 0-10% MeOH in TBME). The resulting residue was dissolved in EtOAc and washed with 1M NaOH, then dried (Na2SO4) and concentrated in vacuo affording 4-{1-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]ethyl}piperidine-1-carboxylic acid benzyl ester (278 mg, 62%) as a white foam. LCMS: RT 4.08 min [M+H]+ 557.5

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (Si-PCC, gradient 0-10% MeOH in TBME)
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed with 1M NaOH
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2d67b3ea5e44b85a5f7b24afabd943e
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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