Triethylamine → HCID 68576616, compound

HRID 2246050Notes

Reaction equation

HRID 2246050 reaction equation
[CH3:1][NH:2][C:3](=[O:28])[C@@H:4]([NH:14][C:15](=[O:27])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24])[C@H:5]([OH:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].C(N(CC)CC)C.[C:36]1([N:42]([CH3:46])[C:43](Cl)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][NH:2][C:3](=[O:28])[C@@H:4]([NH:14][C:15](=[O:27])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[C:23]([F:24])([F:25])[F:26])[C@H:5]([O:13][C:43]([N:42]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:46])=[O:44])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 68576139HCID 68576139, compound

Product 1

HCID 68576616HCID 68576616, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.4 g (0.001 mol) of (2S,3R)—N-methyl-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxy-3-o-tolylpropionamide was dissolved in methylene chloride, 0.13 g (0.0013 mol) of triethylamine and a spatula-tip of 4-dimethylaminopyridine were added, and 0.22 g of N-phenyl-N-methylcarbamoyl chloride in methylene chloride was added dropwise. The suspension was stirred for 15 hours and then extracted with 5% strength hydrochloric acid and NaHCO3 solution and dried. Chromatographic purification (silica gel column, cyclohexane/ethyl acetate) gave 0.28 g of the title compound as a colorless oil.

Workup

  1. extractionextracted with 5% strength hydrochloric acid and NaHCO3 solution
  2. customdried
  3. customChromatographic purification (silica gel column, cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-1a0f1cdbdc7b45708bcdb8c265bb06c1
Source dataset
uspto-grants-2010_03
Patent number
US07687435B2

Reaction notes

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