2-Ethylbutyric acid → HCID 69907473, compound

HRID 382476Notes

Reaction equation

HRID 382476 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH2:17][C@H:18]([N:20]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH2:38][C:39]([F:42])([F:41])[F:40])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])[CH:7]=[C:8]2[C:12]=1[N:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH:10]=[CH:9]2)(=[O:3])[NH2:2].[CH2:43]([CH:45]([CH2:49][CH3:50])[C:46](Cl)=[O:47])[CH3:44].C(C(CC)C(O)=O)C.C(Cl)(=O)C(Cl)=O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH2:43]([CH:45]([CH2:49][CH3:50])[C:46]([O:16][CH2:15][CH2:14][CH2:13][N:11]1[C:12]2[C:8](=[CH:7][C:6]([CH2:17][C@H:18]([N:20]([C:21]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:27])[CH2:28][CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH2:38][C:39]([F:40])([F:41])[F:42])[CH3:19])=[CH:5][C:4]=2[C:1](=[O:3])[NH2:2])[CH:9]=[CH:10]1)=[O:47])[CH3:44]

Participants

7

Reactant 5

HCID 69152-Ethylbutyric acidHCID 65578Oxalyl chlorideHCID 759542-Ethylbutyryl chlorideHCID 516892Sodium BicarbonateHCID 86757539HCID 86757539, compound

Product 1

HCID 69907473HCID 69907473, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-1H-indol-5-yl]-1-methylethyl]-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]carbamate (2.00 g) was dissolved in dry pyridine (3 ml), and 2-ethylbutyryl chloride (0.54 g) prepared from 2-ethylbutyric acid and oxalyl chloride was added to the solution. After the mixture was stirred overnight at room temperature, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine subsequently, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel (eluent:hexane/ethyl acetate=2/1) to give white amorphous (R)-3-[5-[2-[N-(tert-butoxycarbonyl)-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-7-carbamoyl-1H-indol-1-yl]propyl 2-ethylbutyrate (1.66 g).

Workup

  1. additionwas added to the solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine subsequently
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel (eluent:hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2158b88281ae4f99976e5109611b41c7
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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