Dimethylformamide → HCID 68681640, compound

HRID 2353974Notes

Reaction equation

HRID 2353974 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[CH3:20][O:21][C:22](=[O:43])[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:25][C:24]=1[NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>C(OCC)(=O)C>[CH3:20][O:21][C:22](=[O:43])[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([O:30][C:31]([F:34])([F:32])[F:33])=[CH:25][C:24]=1[N:35]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 68679331HCID 68679331, compound

Product 1

HCID 68681640HCID 68681640, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Add methyl 4-bromobutyrate (1.1 g, 6.0 mmol) and cesium carbonate (3.9 g, 12.0 mmol) to a DMF solution of 2-(tert-butoxycarbonylamino)-5-methyl-4-trifluoromethoxy-benzoic acid methyl ester (1.4 g, 4.0 mmol) under nitrogen. After stirring at 60° C. for 5 hours, the reaction mixture is cooled to room temperature and diluted with ethyl acetate (150 mL). Wash the organics with water (2×150 mL) followed by brine (100 mL), dry over sodium sulfate, and filter. Remove the solvent under vacuum and chromatograph the crude product over silica gel using ethyl acetate/hexane (5-30%) to elute. This provides the title compound (1.1 g, 61%) as an oil: H NMR (CDCl3, 400 MHz) δ 1.28 (s, 6H), 1.49 (s, 3H), 1.91 (m, 2H), 2.33 (m, 5H), 3.39 (m, 1H), 3.63 (s, 3H), 3.77 (m, 1H), 3.86 (bs, 3H), 7.06 (m, 1H), 7.80 (m, 1H). MS (ES+): 350 (M+H-100).

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. washWash the organics with water (2×150 mL)
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. customRemove the solvent under vacuum and chromatograph the crude product over silica gel
  6. washto elute

Sources & evidence

ORD record
ord-2e7ed6b01bdb4e759faf0c68da2fc2de
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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