Diisopropylethylamine → HCID 22096198, compound

HRID 2230290Notes

Reaction equation

HRID 2230290 reaction equation
[NH2:1][C@@H:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)[C:3]([NH:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[N:20]1([C:27]([NH:29][C@@H:30]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:31](O)=[O:32])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(Cl)Cl>[C:6]([NH:5][C:3]([CH:2]([NH:1][C:31]([CH:30]([NH:29][C:27]([N:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:28])[CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)=[O:4])([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7530182(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acidHCID 54534915HCID 54534915, compound

Product 1

HCID 22096198HCID 22096198, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The crude product from Example AK ((S)-2-Amino-3-(4-nitrophenyl)-N-tert-butylpropionamide) (1.34 g, 5.25 mmol) and the product from Example Z (1.35 g, 5.25 mmol) were dissolved in DMF (40 mL), then HBTU (1.99 g, 5.25 mmol) and diisopropylethylamine (4.3 g, 33 mol) were added and stirred for 1 hour. The mixture was poured into CH2Cl2 (100 mL); the CH2Cl2 solution was washed with aqueous sodium bicarbonate (3×) and dried over sodium bicarbonate. The crude reaction mixture was further purified by column chromatography (SiO2, EtOAc) to yield the title compound (2.5 g), mp 194-195° C.

Workup

  1. washthe CH2Cl2 solution was washed with aqueous sodium bicarbonate (3×)
  2. dry with materialdried over sodium bicarbonate
  3. customThe crude reaction mixture
  4. customwas further purified by column chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-20d359ffca8749e38e3a2a38a1ba53a7
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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