Sodium Iodide → HCID 14780080, compound

HRID 980964Notes

Reaction equation

[Si:1]([O:8][CH:9]([CH:11]1[CH:14]([S:15][CH3:16])[N:13]([CH:17](Cl)[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[C:12]1=[O:32])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I-].[Na+].C([BH3-])#N.[Na+]>>[Si:1]([O:8][CH:9]([CH:11]1[CH:14]([S:15][CH3:16])[N:13]([CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)=[O:19])[C:12]1=[O:32])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 5238Sodium Iodide

HCID 5003444Sodium cyanoborohydride

HCID 88660712HCID 88660712, compound

Product 1

HCID 14780080HCID 14780080, compoundYield 66.2%

Procedure

Following the procedure of Preparation 3, but using p-nitrobenzyl 2-[3-(1-t-butyldimethylsilyloxyethyl)-4-methylthio-2-azetidinon-1-yl]-2-chloroacetate (1.272 g), sodium iodide (379 mg) and sodium cyanoborohydride (314 mg) and purifying the crude product by silica gel column chromatography eluted with a 10:1 by the volume mixture of benzene and ethyl acetate, there were obtained 785 mg of the desired compound.

Workup

customthe procedure of Preparation 3
custompurifying the crude product by silica gel column chromatography
washeluted with a 10:1 by the volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record: ord-b912c9dc707344db8f8d03055ccb613c
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04639441

Reaction notes

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