Triphenylphosphine → n-{(3s,4s)-2-Oxo-1-(phenylmethoxy)-4-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]azetidin-3-yl}(tert-butoxy)carboxamide

HRID 527380Notes

Reaction equation

HRID 527380 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:21](O)[CH2:22][O:23][Si:24]([CH3:30])([CH3:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([NH:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:11]=[C:10]1[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@@H:21]([CH2:22][O:23][Si:24]([CH3:30])([CH3:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[N:12]1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 866395312-[(tert-butoxy)carbonylamino]-3-hydroxy-N-(phenylmethoxy)-4-(1,1,2,2-tetramethyl-1-silapropoxy)butanamide

Product 1

HCID 67121282n-{(3s,4s)-2-Oxo-1-(phenylmethoxy)-4-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]azetidin-3-yl}(tert-butoxy)carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of THF (1.5 L) containing 2-[(tert-butoxy)carbonylamino]-3-hydroxy-N-(phenylmethoxy)-4-(1,1,2,2-tetramethyl-1-silapropoxy)butanamide (9.8 g, 21.56 mmol), triphenylphosphine (17.5 g, 66.8 mmol) and diethyl azodicarboxylate (11.26 g, 64.7 mmol) was stirred at room temperature for 2 h. The solvent was evaporated in vacuo and the residue was purified under column chromatography using a mixture of ethyl acetate and hexane (1/4) as eluent to obtained 7.25 g of the desired product.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified under column chromatography
  3. additiona mixture of ethyl acetate and hexane (1/4) as eluent

Sources & evidence

ORD record
ord-bfa8c59c7a6d4122a018bdf294f9c221
Source dataset
uspto-grants-2016_05
Patent number
US09346799B2

Reaction notes

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