Triethylamine → HCID 58935420, compound

HRID 2218076Notes

Reaction equation

HRID 2218076 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C@H:8]([NH:17][C:18]([C:20]2([CH2:25][CH:26]([CH2:30][C:31]([N:33]([CH:35]([CH3:37])[CH3:36])[CH3:34])=[O:32])[C:27]([OH:29])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[C:7]1=[O:38])[CH3:2].C(N([CH2:45][CH3:46])CC)C.[C:47]([O-:50])([O-:49])=[O:48].[K+].[K+].[CH3:53][C:54](=O)OCC>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C@H:8]([NH:17][C:18]([C:20]2([CH2:25][CH:26]([CH2:30][C:31]([N:33]([CH:35]([CH3:36])[CH3:37])[CH3:34])=[O:32])[C:27]([O:29][CH:53]([O:48][C:47]([O:50][CH2:45][CH3:46])=[O:49])[CH3:54])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[C:7]1=[O:38])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58935427HCID 58935427, compound

Product 1

HCID 58935420HCID 58935420, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

107 mg of 2-{[1-({[(3S)-1-(2-Ethoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-[isopropyl(methyl)amino]-4-oxobutanoic acid (for preparation see example 72) was dissolved in 1 ml of DMF. Then 83 μl of triethylamine, 20 mg of solid K2CO3 and 85 μl of chloroethylethylcarbonate was added. After stirring over night the mixture was diluted with EA and consecutively washed with an aqueous KHSO4 solution and with brine. Drying of the organic layer over magnesium sulfate and column chromatography on silica gel (liquid phase: EA/cyclohexane 1:1 (v/v)) yielded 41 mg of the title compound as a white foam, MS: [M+H]+: 660; m/z: 526, 449, 310, 253.

Workup

  1. washconsecutively washed with an aqueous KHSO4 solution and with brine
  2. dry with materialDrying of the organic layer over magnesium sulfate and column chromatography on silica gel (liquid phase: EA/cyclohexane 1:1 (v/v))

Sources & evidence

ORD record
ord-35c1aeaea8d1421b9a45f950cbc107a4
Source dataset
uspto-grants-2008_08
Patent number
US07410962B2

Reaction notes

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