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Triphenylphosphine → HCID 68313033, compound

HRID 1530387
Notes
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Reaction equation

HRID 1530387 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([O:20][C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)[CH2:18]C)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N1CCC(C(O)C)CC1)=O)C1C=CC=CC=1.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>O1CCOCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH:17]([O:20][C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:40])[CH3:41])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)[CH3:18])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 18918437Phenylmethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylateHCID 68312705HCID 68312705, compound

Product 1

HCID 68313033HCID 68313033, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol from Example 4 (400 mg, 1.23 mmol), 4-(1-hydroxyethyl)piperidine-1-carboxylic acid benzyl ester (487 mg, 1.85 mmol) and triphenylphosphine (548 mg, 2.09 mmol) in dioxane (7 mL) was added dropwise DIAD (410 ul, 2.09 mmol) and the reaction mixture was stirred at RT for 18 h. The mixture was then diluted with EtOAc and washed with aq. NaOH (1N). The aqueous phase was extracted with EtOAc (×3) and the combined organic layers were then washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc), then suspended in DCM and filtered. The filtrate was concentrated in vacuo and purified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM) affording 4-{1-[2-(2-Isopropyl-5-methyl-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 (140 mg, 20%). LCMS: RT 3.90 min [M+H]+ 571.0

Workup

  1. washwashed with aq. NaOH (1N)
  2. extractionThe aqueous phase was extracted with EtOAc (×3)
  3. washthe combined organic layers were then washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. custompurified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-12956316429545abb718aee1a48d4a17
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090628B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes