Sodium Bicarbonate → HCID 68485154, compound

HRID 1896981Notes

Reaction equation

HRID 1896981 reaction equation
Cl.C(S[C:7]1[CH:8]=[C:9]([CH:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][NH:15][CH2:16][C:17]([N:19]([CH3:21])[CH3:20])=[O:18])[CH:10]=[CH:11][CH:12]=1)CCC.Cl.[CH2:30](SC1C=C(CCNCC(N(C)C)=O)C=CC=1)[CH2:31][CH2:32][CH3:33].O[O:51][S:52]([O-:54])=O.[K+].C([O-])(O)=O.[Na+]>C(#N)C.O>[CH2:30]([S:52]([C:7]1[CH:8]=[C:9]([CH:13]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:14][NH:15][CH2:16][C:17]([N:19]([CH3:20])[CH3:21])=[O:18])[CH:10]=[CH:11][CH:12]=1)(=[O:54])=[O:51])[CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68483348HCID 68483348, compoundHCID 131730831HCID 131730831, compound

Product 1

HCID 68485154HCID 68485154, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-[2-(3-butylthiophenyl)-(tert-butoxycarbonyl)ethylamino]-N,N-dimethylacetamide hydrochloride (0.25 g, 0.62 mmol; prepared from the compound of Step 2 of Example 7, by reaction with boc2O according to the procedure described in the first part of Step 1 of Example 1) in acetonitrile (20 ml)/water (10 ml), a mixture of oxone (0.92 g, 1.5 mmol) and NaHCO3 (0.2 g, 2.3 mmol) was added portionwise over 5 minutes. The mixture was stirred at room temperature for 2 h. The mixture was partitioned between water and CH2Cl2, the organic was washed with water and brine, dried over Na2SO4 and the solvent was evaporated under reduced pressure. The crude was purified by flash chromatography (petroleum ether:AcOEt 3:7) to give pure title compound as a colourless oil (0.20 g, 75% yield).

Workup

  1. additionwas added portionwise over 5 minutes
  2. customThe mixture was partitioned between water and CH2Cl2
  3. washthe organic was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude was purified by flash chromatography (petroleum ether:AcOEt 3:7)

Sources & evidence

ORD record
ord-4216d221cd784b4591bfe4a51863697d
Source dataset
uspto-grants-2013_08
Patent number
US08519000B2

Reaction notes

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