Diethylamine → 5-(1-Diethylcarbamoyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966501Notes

Reaction equation

HRID 966501 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][C:21]([C:24]([OH:26])=O)([CH3:23])[CH3:22])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCCCCC.C(OCC)(=O)C>C(OC(=O)C)C>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][C:21]([C:24](=[O:26])[N:30]([CH2:31][CH3:32])[CH2:28][CH3:29])([CH3:22])[CH3:23])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21226206Ethyl acetate hexaneHCID 233938135-(1-Carboxy-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 101592625-(1-Diethylcarbamoyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterYield 12%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(1-Carboxy-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.0 g, 2.76 mmol, 1.0 eq) was dissolved in ethylacetate (100 mL), and treated with diethylamine (0.241 g, 3.3 mmol, 1.2 eq) followed by HBTU (0.446 g, 3.3 mmol, 1.2 eq). The reaction mixture was stirred at room temperature for 24 hours and was followed by TLC (hexane/ethyl acetate 1/1). The reaction was quenched with aqueous sodium bicarbonate, extracted with ethyl acetate, and the organic layers dried over sodium sulfate, evaporated, and loaded on silica gel, followed by flash chromatography (hexane/ethyl acetate 1/1). 0.109 g of the product was obtained, 12% yield. LC/MS (ESI+) 422.52 (M+1) (C25H30N2O4).

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layers dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-aec778a9fa7045b5b5bd9e8ea0a68821
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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