Sodium Iodide → 2-tert-Butoxycarbonylamino-3-fluorobenzoic acid 2-(tert-butyldimethylsilanyloxy)ethyl ester

HRID 558979Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([NH:14][C:15]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:13])([CH3:10])([CH3:9])[CH3:8].Br[CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].[I-].[Na+]>CN(C=O)C>[Si:29]([O:28][CH2:27][CH2:26][O:18][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:15]=1[NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of caesium carbonate (1.63 g, 5.0 mmol) in DMF (10 ml) was added 2-tert-butoxycarbonylamino-3-fluoro-benzoic acid from Example 19A (1.15 g, 4.5 mmol), (2-bromoethoxy)-tert-butyldimethylsilane (1.08 g, 4.5 ml) and sodium iodide (680 mg, 4.5 ml). The mixture was heated at 65° C. for 3 h and evaporated in vacuo. The residue was partitioned between chloroform and brine and the organic phase was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc: pet. ether 15:85) to give a colourless gum; yield 1.1 g, 59%.

Workup

customevaporated in vacuo
customThe residue was partitioned between chloroform and brine
customthe organic phase was dried
customevaporated in vacuo
customThe residue was purified by flash chromatography on silica (eluant EtOAc: pet. ether 15:85)
customto give a colourless gum

Sources & evidence

ORD record: ord-35117737a53d48448db48207bb042bd9
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063038B2

Reaction notes

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