Triphenylphosphine → HCID 118379892, compound

HRID 708531Notes

Reaction equation

HRID 708531 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, 1.61 mmol), tert-butyl(3-hydroxypropyl)carbamate (282 mg, 1.611 mmol) and triphenylphosphine (634 mg, 2.42 mmol) in THF (16 mL) was added DIAD (470 μl, 2.42 mmol). The mixture was stirred at room temperature for 16 h, whereupon the volatiles were removed in vacuo. Purification via silica gel chromatography (EtOAc-Heptane, 0-100%) afforded the title compound (600 mg, 80%). LCMS: Rt=1.02 min, m/z=468.4 (M+1) Method 2m_acidic.

Workup

  1. customwere removed in vacuo
  2. customPurification via silica gel chromatography (EtOAc-Heptane, 0-100%)

Sources & evidence

ORD record
ord-55bd7633e1a042bf89b838eea591bd21
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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