Diisopropylethylamine → HCID 68921013, compound

HRID 1191292Notes

Reaction equation

HRID 1191292 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[CH:16]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50]([C:53](O)=[O:54])[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[CH:16]3[CH2:27][CH2:28][N:29]([CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:53]([CH:50]3[CH2:51][CH2:52][N:47]([C:45]([O:44][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:46])[CH2:48][CH2:49]3)=[O:54])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68917835HCID 68917835, compound

Product 1

HCID 68921013HCID 68921013, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound 29 (89 mg), dimethylformamide (1 mL), 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (44 mg), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (94 mg) and diisopropylethylamine (42 μL) were stirred at room temperature for overnight. The reaction solution was added aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol:aqueous ammonia=80:20:1) to obtain the title compound (56 mg) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol:aqueous ammonia=80:20:1)

Sources & evidence

ORD record
ord-434382d73afe476da7b5345d6e2d3361
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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