Water → HCID 68487077, compound

HRID 1770652Notes

Reaction equation

HRID 1770652 reaction equation
[H-].[Na+].[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][NH2:16])[CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][CH3:6].Cl[CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27].O>CN(C=O)C>[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:15][NH:16][CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 68485070HCID 68485070, compound

Product 1

HCID 68487077HCID 68487077, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60%, 2.0 g, 51 mmol) in dry DMF (125 ml) cooled at 0° C., a solution of 2-(3-butoxyphenyl)-(tert-butoxycarbonyl)ethylamine (7.5 g, 25.5 mmol) in dry DMF (125 ml) was added dropwise. After 1 h at room temperature, 2-chloro-N,N-dimethylacetamide (5.2 ml, 51 mmol) was added and the mixture was stirred for 16 h at room temperature. H2O (10 ml) was added and the solvent was evaporated under reduced pressure. The residue was dissolved in H2O (150 ml) and extracted with CH2Cl2 (2×150 ml). The collected organic phases were dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (petroleum ether/EtOAc 4:6) affording the title compound (7.2 g, 75%) as light yellow oil. 1H NMR (300 MHz, DMSO-d6): δ 7.1 (m, 1H), 6.79-6.71 (m, 3H), 3.97 (t, J=6.0 Hz, 2H), 3.96 (s, 2H), 3.40 (dd, J=8.7 Hz, J=7.2 Hz, 2H), 2.88 (s, 6H), 2.76 (dd, J=7.9 Hz, J=6.4 Hz, 2H), 1.76 (m, 2H), 1.46 (m, 2H), 1.37 (s, 9H), 0.95 (t, J=7.3 Hz, 3H).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in H2O (150 ml)
  3. extractionextracted with CH2Cl2 (2×150 ml)
  4. dry with materialThe collected organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified by flash chromatography (petroleum ether/EtOAc 4:6)

Sources & evidence

ORD record
ord-7b5ff800a27a4e13968bc97735ef1a86
Source dataset
uspto-grants-2016_02
Patent number
US09248116B2

Reaction notes

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