Methyl chloroformate → [2-[[2,6-bis(1-Methylethyl)phenyl]amino]-2-oxoethyl](diphenylmethyl)carbamic acid methyl ester

HRID 465653Notes

Reaction equation

HRID 465653 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].[CH3:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:10]=1[NH:18][C:19](=[O:35])[CH2:20][NH:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:8].CCN(CC)CC>C1COCC1.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH3:1][O:2][C:3](=[O:4])[N:21]([CH2:20][C:19]([NH:18][C:10]1[C:9]([CH:7]([CH3:6])[CH3:8])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:15]([CH3:17])[CH3:16])=[O:35])[CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 6586Methyl chloroformate2×HCID 8471TriethylamineHCID 1645639N-[2,6-bis(1-Methylethyl)phenyl]-2-[(diphenylmethyl)amino]acetamide

Product 1

HCID 67904661[2-[[2,6-bis(1-Methylethyl)phenyl]amino]-2-oxoethyl](diphenylmethyl)carbamic acid methyl ester

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Several milliliters of methylchloroformate was added to the product from Example 4 (0.60 g) in a mixture of excess NEt3 and EtOAc at room temperature. Vigorous outgassing occurred with the formation of a precipitate. The solution was stripped to dryness and the residue taken up in a mixture of 50 mL THF and 50 mL saturated NaHCO3 solution. Excess methyl chloroformate was added at room temperature. This solution was allowed to sit 5 days at room temperature. The reaction mixture was diluted with EtOAc and washed with aqueous K2CO3 solution and aqueous NaCl solution. The organic layer was dried over MgSO4, filtered, and concentrated to a white solid. The solid was slurried in hexane/EtOAc 9/1 and collected by filtration. 0.55 g (80%). NMR (CDCl3) δ 1.06 (12H, d), δ 2.56 (2H, m), δ 3.84 (3H, s), δ 4.20 (2H, s), δ 6.80 (1H, bs), δ 7.0-7.5 (13H, m). IR (KBr) 3443, 2963, 1705, 1685, 699 cm-1.

Workup

  1. washwashed with aqueous K2CO3 solution and aqueous NaCl solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a white solid
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-995b416a9b45407fadb267e1a7c32a11
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

Loading…