Chloride → t-Butyl 2-[(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydrofuran-3-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate

HRID 376578Notes

Reaction equation

HRID 376578 reaction equation
O[CH:2]([N:10]1[C@H:13]([S:14][CH2:15][C:16]([CH:18]2[CH2:22][CH2:21][O:20][CH2:19]2)=[O:17])[C@H:12]([NH:23][C:24](=[O:32])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:11]1=[O:33])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].S(Cl)(Cl)=O.N1[C:43]([CH3:44])=[CH:42][CH:41]=CC=1C.[Cl-].[CH2:47]([PH2:51])[CH2:48][CH2:49][CH3:50]>C1COCC1.O1CCOCC1>[C:26]1([CH2:25][C:24]([NH:23][C@H:12]2[C@@H:13]([S:14][CH2:15][C:16]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)=[O:17])[N:10]([C:2](=[P:51]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:15][CH2:16][CH2:18][CH3:19])[CH2:47][CH2:48][CH2:49][CH3:50])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:11]2=[O:33])=[O:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 312ChlorideHCID 79372,6-LutidineHCID 24386Thionyl ChlorideHCID 2784062ButylphosphineHCID 53961123t-Butyl (RS)-2-hydroxy-2-[(3R, 4R)-3-phenylacetamido-4-[(RS)-tetrahydrofuran-3-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate

Product 1

HCID 18396316t-Butyl 2-[(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydrofuran-3-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

t-Butyl (RS)-2-hydroxy-2-[(3R, 4R)-3-phenylacetamido-4-[(RS)-tetrahydrofuran-3-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate (2.719g) in THF (20ml) was treated with thionyl chloride (1.01g, 0.615ml) and 2,6-lutidine (0.913g, 0.989ml) as described in Example 1(d). Following work-up the crude chloride in dioxan (30ml) was then treated with n-butylphosphine (2.53g, 3.11ml). After purification by flash chromatography with 50, 70% ethyl acetate/hexane then ethyl acetate the title compound was obtained as a pale yellow foam (1.496 g, 40%); vmax (CH2Cl2) 3420, 1762, 1717 (shoulder), 1681 and 1625cm-1. (Mass spectrum: +ve ion (3NOBA, Na+), MH+ (663), MNa+ (685)).

Workup

  1. customAfter purification by flash chromatography with 50, 70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-07d9463182334892932a5902cd64c10e
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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