Water → HCID 118221098, compound

HRID 1507198Notes

Reaction equation

HRID 1507198 reaction equation
[I-].[C:2]([O:6][C:7]([NH:9][C@@H:10]([C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)=[O:17])[CH2:11][CH2:12][S+](C)C)=[O:8])([CH3:5])([CH3:4])[CH3:3].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl-].[NH4+].O>C1COCC1>[C:2]([O:6][C:7](=[O:8])[NH:9][C@@H:10]1[CH2:11][CH2:12][N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:16]1=[O:17])([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 131734367HCID 131734367, compound

Product 1

HCID 118221098HCID 118221098, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of (R)-(3-((tert-butoxycarbonyl)amino)-4-((3,4-dimethoxybenzyl)amino)-4-oxobutyl)dimethylsulfonium, iodide salt (2 g, 3.7 mmol) in THF (50 mL) was added LHMDS (3.7 mL, 3.7 mmol) dropwise. The reaction was stirred at 0° C. for a further 2 hrs. Then was added saturated ammonium chloride solution and water. The mixture was extracted with 100 mL ethyl acetate. The layers were separated and the organic fraction was washed with water and brine. It was then dried over sodium sulfate, filtered, and evaporated. The residue was purified via silica gel chromatography using 50% ethyl acetate/petroleum ether. Yield 0.8 gms (R)-tert-butyl(1-(3,4-dimethoxybenzyl)-2-oxopyrrolidin-3-yl)carbamate. LCMS (method P) RT 0.82 min, m/z 351.2 (MH+); 1H NMR (400 MHz, chloroform-d) δ 1.45 (s, 9H), 1.78-1.86 (m, 1H), 2.57-2.60 (br s, 1H), 3.15-3.23 (m, 2H), 3.68 (s, 6H), 4.12-4.25 (br s, 1H), 4.40 (m, 2H), 5.14 (br s, 1H), 6.75-6.82 (m, 3H).

Workup

  1. extractionThe mixture was extracted with 100 mL ethyl acetate
  2. customThe layers were separated
  3. washthe organic fraction was washed with water and brine
  4. dry with materialIt was then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified via silica gel chromatography
  8. customLCMS (method P) RT 0.82 min, m/z 351.2 (MH+)

Sources & evidence

ORD record
ord-e088ecd8d8ec4ad98b1fa7de63f80cf9
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

Loading…