Triphenylphosphine → HCID 118379892, compound

HRID 708518Notes

Reaction equation

HRID 708518 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]([O:27][C:28](=[O:34])[NH:29][CH2:30][CH2:31][CH2:32]O)([CH3:26])([CH3:25])[CH3:24].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:23]([O:27][C:28]([NH:29][CH2:30][CH2:31][CH2:32][N:15]([C:9](=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:34])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 118379892HCID 118379892, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of tert-butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate (500 mg, 1.611 mmol), tert-butyl(3-hydroxypropyl)carbamate (282 mg, 1.611 mmol) and triphenylphosphine (634 mg, 2.417 mmol) dissolved in THF (16 mL) was added DIAD (470 μl, 2.417 mmol) and stirred for 16 h. The reaction mixture was concentrated in vacuo and the crude residue was purified via silica gel chromatography (EtOAc-Heptane) to afford the title compound (600 mg, 80%). LCMS: Rt=1.02 min, m/z=468.4 (M+1) Method 2m_acidic.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude residue was purified via silica gel chromatography (EtOAc-Heptane)

Sources & evidence

ORD record
ord-3a8d1a893eeb466abb76065f67888da7
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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