Triphenylphosphine → HCID 118379264, compound

HRID 708525Notes

Reaction equation

HRID 708525 reaction equation
O[CH:2]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][C@@H:10]2[C@H:13]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12](=[O:25])[NH:11]2)[N:5]=1)[CH3:3].[C:26]([O:30][C:31](/[N:33]=[C:34](\[NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])/[N:35]1[CH:39]=[CH:38][CH:37]=[N:36]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].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>[CH2:17]([O:16][C:15]([NH:14][C@@H:13]1[C:12](=[O:25])[NH:11][C@@H:10]1[CH2:9][N:6]1[N:5]=[C:4]([CH:2]([N:40](/[C:34](=[N:33]/[C:31]([O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:32])/[N:35]2[CH:39]=[CH:38][CH:37]=[N:36]2)[C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH3:3])[CH:8]=[N:7]1)=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 6107782HCID 6107782, compoundHCID 131733836HCID 131733836, compound

Product 1

HCID 118379264HCID 118379264, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(1-hydroxyethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (460 mg, 1.33 mmol), (E)-tert-butyl (((tert-butoxycarbonyl)imino)(1H-pyrazol-1-yl)methyl)carbamate (455 mg, 1.465 mmol), and triphenylphosphine (419 mg, 1.60 mmol) in THF (7 ml) at 0° C. was added DIAD (0.311 ml, 1.598 mmol) dropwise. The reaction was stirred at room temperature overnight and concentrated to dryness. Purification of the crude residue via silica gel chromatography (EtOAc-Heptane, 30-60%) afforded the title compound (190 mg, 22%) as a light yellow solid. LCMS: Rt=0.99 min, m/z=638.4 (M+1) Method 2m_acidic.

Workup

  1. concentrationconcentrated to dryness
  2. customPurification of the crude residue via silica gel chromatography (EtOAc-Heptane, 30-60%)

Sources & evidence

ORD record
ord-b114eab5240a4897a2c25094193d1442
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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