Sodium Iodide → HCID 54003150, compound

HRID 1460727Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

Into 5 ml of dry acetonitrile were suspended 263 mg (1 millimole) of p-nitrobenzyl 2-diazoacetoacetate, 226 mg (1.5 millimoles) of tertbutyldimethylsilyl chloride and 210 mg (1.4 millimoles) of sodium iodide. To the mixture was added 220 μl (1.6 millimoles) of triethylamine under an argon atmosphere at a room temperature. The resultant was heated up to 40° C. and agitated at the same temperature overnight, followed by concentration under a reduced pressure. To the residue was added 20 ml of ethyl acetate, and the resultant was washed twice with 10 ml portions of water. The organic layer was dried and then concentrated to dryness under a reduced pressure to give 340 mg (yield 90%) of the desired compound in a yellow solid. The physical properties of the product were in agreement with those of the product obtained in Example 2.

Workup

concentrationfollowed by concentration under a reduced pressure
additionTo the residue was added 20 ml of ethyl acetate
washthe resultant was washed twice with 10 ml portions of water
customThe organic layer was dried
concentrationconcentrated to dryness under a reduced pressure

Sources & evidence

ORD record: ord-845d709b25cb404cbdbe48a3a6b3b96a
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071966

Reaction notes

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