Sodium Carbonate → HCID 66810793, compound

HRID 227344Notes

Reaction equation

HRID 227344 reaction equation
C([CH:9]([O:16][C:17]([NH:19][CH2:20][C:21]1([CH2:27][C:28]([O:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.[CH:35]1[CH:40]=[C:39](Cl)[CH:38]=[C:37]([C:42]([O:44]O)=[O:43])[CH:36]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:42]([O:44][CH:9]([O:16][C:17]([NH:19][CH2:20][C:21]1([CH2:27][C:28]([O:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 668108572-Cyanoethyl 1-{[(alpha-Benzoylbenzyloxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

Product 1

HCID 66810793HCID 66810793, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-cyanoethyl 1-{[(α-benzoylbenzyloxy)carbonyl]aminomethyl}-1-cyclohexane acetate (9) (115 mg, 0.248 mmol) in 4 mL of CH2Cl2 was added to a mixture of mCPBA (77%, 111 mg, 0.497 mmol) and Na2CO3 (52.7 mg, 0.497 mmol) at room temperature. The resulting suspension was stirred at room temperature with TLC monitoring. After completion of the reaction (about 8 hours) the reaction mixture was diluted with CH2Cl2, washed with saturated NaHCO3 solution and brine and dried over Na2SO4. After concentration in vacuo the residue was purified on silica gel (40% ethyl acetate in hexane) to afford 89 mg (75%) of the title compound. 1H NMR (CDCl3): δ 8.08 (2H, dd, J=6.8, 1.6 Hz); 7.91 (1H, s); 7.63-7.54 (3H, m); 7.44-7.40 (5H, m); 5.42 (1H, t, J=6.4 Hz); 4.22 (2H, t, J=6.2 Hz); 3.25 (2H, dd, J=6.4, 4.6 Hz); 2.65 (2H, t, J=6.2 Hz); 2.35 (2H, s); 1.53-1.37 (10H, m). 13C NMR (CDCl3): δ 172.11; 164.73; 154.75; 136.29; 133.70; 130.18; 129.85; 129.63; 128.85; 128.68; 126.85; 117.11; 91.41; 58.94; 47.93; 10.06; 38.09; 34.15; 26.00; 21.55; 18.16.

Workup

  1. customAfter completion of the reaction (about 8 hours) the reaction mixture
  2. washwashed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration in vacuo the residue
  5. customwas purified on silica gel (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-771441c3d214411eb283d1bd21c044ae
Source dataset
uspto-grants-2009_07
Patent number
US07560483B2

Reaction notes

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