Sodium Carbonate → HCID 57905223, compound

HRID 1093059Notes

Reaction equation

HRID 1093059 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH:15]([NH:18][CH3:19])[C:16]#[N:17])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>C1COCC1.O>[Si:1]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH:15]([C:16]#[N:17])[N:18]([CH3:19])[C:27](=[O:28])[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 57904874HCID 57904874, compound

Product 1

HCID 57905223HCID 57905223, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 2-(3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl)-2-(methylamino)acetonitrile (6.0 g, 21.24 mmol) in THF (33 mL), H2O (15 mL) was added, at 0, ° C. Na2CO3 (4.50 g, 42.48 mmol) followed by the dropwise addition of benzyl chloroformate (3.89 mL, 27.6 mmol) over 10 min. The reaction mixture was stirred at 0° C. for 30 min. then at 23° C. for 18 hours. H2O (150 mL) was then added and the organic material was extracted with ethyl acetate (3×100 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The crude material was purified on a Silica gel column (Biotage flash chromatography system), eluted with a gradient of ethyl acetate:hexane (1:4) to (1:1) to afford 3.90 g (44% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.34-7.45 (5 H, m), 5.33 (2 H, s), 5.18-5.25 (1H, m), 3.48-3.59 (2 H, m), 3.00 (3 H, s), 2.35-2.47 (2 H, m), 1.55-2.25 (6 H, m), 0.94 (9 H, s), 0.05 (6 H, s). LCMS (+ESI, M+H+) m/z 417.

Workup

  1. waitat 23° C. for 18 hours
  2. extractionthe organic material was extracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified on a Silica gel column (Biotage flash chromatography system)
  6. washeluted with a gradient of ethyl acetate:hexane (1:4) to (1:1)

Sources & evidence

ORD record
ord-03a44139984241f0a6202b1dd3712dfe
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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