Chloride → 4-Methoxybenzyl 2-[(3R,4R)-3-Phenylacetamido-4-[(2RS, 3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate

HRID 1421835Notes

Reaction equation

HRID 1421835 reaction equation
O[CH:2]([N:15]1[C@H:18]([S:19][CH2:20][C:21]([CH:23]2[CH:27]([CH3:28])[CH2:26][CH2:25][O:24]2)=[O:22])[C@H:17]([NH:29][C:30](=[O:38])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:16]1=[O:39])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4].[Cl-].S(Cl)(Cl)=O.N1C(C)=CC=CC=1C.[CH2:53]([P:57]([CH2:62][CH2:63][CH2:64][CH3:65])[CH2:58][CH2:59][CH2:60][CH3:61])[CH2:54][CH2:55][CH3:56]>O1CCCC1.O1CCOCC1>[C:32]1([CH2:31][C:30]([NH:29][C@H:17]2[C@@H:18]([S:19][CH2:20][C:21]([CH:23]3[CH:27]([CH3:28])[CH2:26][CH2:25][O:24]3)=[O:22])[N:15]([C:2](=[P:57]([CH2:58][CH2:59][CH2:60][CH3:61])([CH2:62][CH2:63][CH2:64][CH3:65])[CH2:53][CH2:54][CH2:55][CH3:56])[C:3]([O:5][CH2:6][C:7]3[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=3)=[O:4])[C:16]2=[O:39])=[O:38])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

8

Reactant 5

HCID 312Chloride2×HCID 79372,6-LutidineHCID 13831TributylphosphineHCID 24386Thionyl ChlorideHCID 867549534-Methoxybenzyl (2RS)-2-Hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(2RS, 3SR)-3-methyltetrahYdrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate

Product 1

HCID 867551054-Methoxybenzyl 2-[(3R,4R)-3-Phenylacetamido-4-[(2RS, 3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetateYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(2RS,3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate (10.406 g) was converted to it's chloride with thionyl chloride (3.34 g, 2.02 ml) and 2,6-lutidine (3.009, 3.25 ml) in tetrahydrofuran (100 ml) as described in Example 6(c). The crude chloride in dioxan (80 ml) was then converted to the product with tri-n-butylphosphine (6.98 ml) also described in 6(c). Flash chromatography on silica gel afforded the title compound as a foam (6.525 g, 47%). [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (763)].

Sources & evidence

ORD record
ord-e41f3005371d4992ae3e9bd2a992ad99
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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