Pivaloyl chloride → HCID 12074058, compound

HRID 382471Notes

Reaction equation

HRID 382471 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][CH3:39])[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])[CH2:10][CH2:9]2)(=[O:3])[NH2:2].[C:40](Cl)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:40]([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][CH3:39])[CH3:19])=[CH:5][C:4]=2[C:1](=[O:3])[NH2:2])[CH2:9][CH2:10]1)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 12074057HCID 12074057, compound

Product 1

HCID 12074058HCID 12074058, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-2,3-dihydro-1H-indol-5-yl]-1-methylethyl]-N-[2-(2-ethoxyphenoxy)ethyl]carbamate (6.24 g) was dissolved in dry pyridine (9.4 ml), and pivaloyl chloride (1.54 ml) was added to the solution. The mixture was stirred overnight at room temperature, and a saturated aqueous sodium bicarbonate solution was added to the reaction mixture. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by column chromatography on aminopropyl silica gel (eluent:hexane/ethyl acetate=1/1) to give colorless amorphous (R)-3-[5-[2-[N-(tert-butoxycarbonyl)-N-[2-(2-ethoxyphenoxy)ethyl]amino]-propyl]-7-carbamoyl-2,3-dihydro-1H-indol-1-yl]propyl pivalate (4.30 g).

Workup

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

Sources & evidence

ORD record
ord-19a189c41b0c473db81101032bff7630
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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