Triphenylphosphine → (3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidine

HRID 279809Notes

Reaction equation

HRID 279809 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:23])[C@H:11]([C@@H:20]([CH3:22])O)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:1]([O:8][N:9]1[C@@H:20]([CH3:22])[C@H:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18598709N-Benzyloxy-t-butoxycarbonyl-threonine amide

Product 1

HCID 12946599(3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidineYield 114.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 12.67 g of N-benzyloxy-t-butoxycarbonyl-threonine amide, 11.5 g of triphenylphosphine, and 6.23 ml of diethylazodicarboxylate in 380 ml of tetrahydrofuran was stirred under nitrogen for about 16 hours. The solution was evaporated and chromatographed on a 900 g silica gel column. Elution with chloroform-ethyl acetate (3:1) gave 13.69 g of compound that crystallized from ether-hexane to yield 9.18 g of the title compound.

Workup

  1. customThe solution was evaporated
  2. customchromatographed on a 900 g silica gel column
  3. washElution with chloroform-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-4501d47b513b4092a516add48c705d4c
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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