Sodium hydride → HCID 23352258, compound

HRID 1899392Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]([O:7][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:9])([CH3:6])[CH3:5].[Br:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[C:28]([CH2:30]Br)[CH:29]=1)[C:23]([O:25][CH3:26])=[O:24].[Cl-].[NH4+]>CN(C)C=O>[CH3:26][O:25][C:23](=[O:24])[C:22]1[CH:27]=[C:28]([CH2:30][N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:8]([O:7][C:4]([CH3:3])([CH3:5])[CH3:6])=[O:9])[CH:29]=[C:20]([CH2:19][Br:18])[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of sodiumhydride (3.6 g, 90mmol) and N,N-dimethylformamide (150 ml) was cooled to 0° C. and treated with solid di-tert-butyliminodicarboxylate (17.4 g, 76.0 mmol) with vigorous stirring. The mixture was stirred at 0° C. for 15 minutes, the ice bath was removed and a solution of methyl 3,5-bis(bromomethyl)-benzoate (23.6 g, 73.2 mmol) in N,N-dimethylform was added dropwise over 30 minutes. After 12 hours the mixture was poured into 100 ml 1/4 saturated aqueous ammonium chloride and extracted with the three 100 ml portion of hexanes. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure and chromatographed using a gradient of 10-20% ethyl acetate/hexanes to yield the product (22.0 g, 66% yield). TLC (20% ethyl acetate/hexanes): Rf =0.55 (UV active, CAM stain)

Workup

customthe ice bath was removed
extractionextracted with the three 100 ml portion of hexanes
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customchromatographed

Sources & evidence

ORD record: ord-c2be04f680b14b5f971340a9b7e79b6c
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571911

Reaction notes

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