Methyl chloroformate → HCID 15480950, compound

HRID 963539Notes

Reaction equation

HRID 963539 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:15][N:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([CH2:23][OH:24])[CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:15][N:14]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([CH2:23][OH:24])[CH2:12][N:11]1[C:26]([O:28][CH3:29])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 15480949HCID 15480949, compound

Product 1

HCID 15480950HCID 15480950, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5 (1.67 g, 5.11 mmol) in acetonitrile (20 mL) was treated with a solution of methyl chloroformate (0.532 g, 5.63 mmol) in acetonitrile (10 mL) at 0° C. The mixture was stirred at ambient temperature for 30 min and then aqueous sodium carbonate solution (15 mL) was added. The organic solvent was removed, and the aqueous residue was extracted with chloroform (3×10 mL). The combined organic extracts were washed with aqueous sodium carbonate solution (10 mL), dried, and evaporated to give 6 (1.52 g. 77.3% yield) as an oil. 1H NMR (CDCl3) δ2.54 (dd, 2H, CH2), 2.45 (t, 1H, OH), 2.72 (dd, 2H, CH2), 3.51 (dd, 2H, CH2), 3.67 (dd, 2H, CH2), 3.69 (s, 3H, OMe), 3.81 (dd, 2H, CH2), 4.44 (dd, 2H, CH2 benzylic), 7.17-7.31 (10H, ArH).

Workup

  1. customThe organic solvent was removed
  2. extractionthe aqueous residue was extracted with chloroform (3×10 mL)
  3. washThe combined organic extracts were washed with aqueous sodium carbonate solution (10 mL)
  4. customdried
  5. customevaporated
  6. customto give 6 (1.52 g. 77.3% yield) as an oil

Sources & evidence

ORD record
ord-3eaec5f8d6cc4ad19b4bccb22f25aa67
Source dataset
uspto-grants-1998_06
Patent number
US05763445

Reaction notes

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