Triphenylphosphine → benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-(aminomethyl)-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

HRID 708481Notes

Reaction equation

HRID 708481 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@H:8]([NH:9][C:10](=[O:46])/[C:11](=[N:25]\[O:26][C:27]2([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH2:29][CH2:28]2)/[C:12]2[N:13]=[C:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[S:15][CH:16]=2)[C:7](=[O:47])[NH:6]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CO>[NH2:1][CH2:4][C@@H:5]1[C@H:8]([NH:9][C:10](=[O:46])/[C:11](=[N:25]\[O:26][C:27]2([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH2:29][CH2:28]2)/[C:12]2[N:13]=[C:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[S:15][CH:16]=2)[C:7](=[O:47])[NH:6]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 118379730benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-(azidomethyl)-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

Product 1

HCID 118380072benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-(aminomethyl)-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylateYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydryl 1-(((Z)-(2-(((2R,3S)-2-(azidomethyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate (689 mg, 1.04 mmol) in THF (10 mL) and MeOH (1.3 mL) was added Ph3P (301 mg, 1.15 mmol). After 12 h, the reaction mixture was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 0-100%) to afford the title compound (369 mg, 56%). LCMS: Rt=0.88 min, m/z=635.1 (M+1), Method 2m_acidic.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 0-100%)

Sources & evidence

ORD record
ord-84eaf213f7154553883e94ac182266ce
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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