Triphenylphosphine → Benzyl((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate

HRID 708522Notes

Reaction equation

HRID 708522 reaction equation
[Si:1]([O:18][CH:19]([C:21]1[N:22]=[N:23][NH:24][CH:25]=1)[CH3:20])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:29]=1[CH2:30][N:31]1[C:34](=[O:35])[C@@H:33]([NH:36][C:37](=[O:46])[O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:32]1[CH2:47]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Si:1]([O:18][CH:19]([C:21]1[CH:25]=[N:24][N:23]([CH2:47][C@@H:32]2[C@H:33]([NH:36][C:37](=[O:46])[O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34](=[O:35])[N:31]2[CH2:30][C:29]2[CH:49]=[CH:50][C:51]([O:53][CH3:54])=[CH:52][C:28]=2[O:27][CH3:26])[N:22]=1)[CH3:20])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13470815benzyl ((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamateHCID 1784771794-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-1,2,3-triazole

Product 1

HCID 131733834Benzyl((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamateYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-1,2,3-triazole (2.42 g, 6.88 mmol), benzyl ((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate (2.76 g, 6.88 mmol), and PPh3 (2.17 mg, 8.26 mmol) in THF (35 ml) at 0° C. was added DIAD (1.60 ml, 8.26 mmol) dropwise. The reaction was stirred at room temperature for 5 h then concentrated in vacuo. Purification of the crude residue via silica gel chromatography (EtOAc-Heptane, 30-60%) afforded the title compound (4.32 g, 85%) as a solid. LCMS: Rt=1.12 min, m/z=734 (M+1) Method 2m_acidic.

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification of the crude residue via silica gel chromatography (EtOAc-Heptane, 30-60%)

Sources & evidence

ORD record
ord-361a94ccc866433685279b2e365b7920
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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