Diisopropylethylamine → HCID 66855115, compound

HRID 1970615Notes

Reaction equation

HRID 1970615 reaction equation
[CH:1]1([NH:5][C:6]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13](=[O:30])[CH2:14][O:15][C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=[C:18]([C:27](O)=[O:28])[CH:17]=2)=[O:7])[CH2:4][CH2:3][CH2:2]1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[C:51]([O:55][C:56](=[O:63])[C@H:57]([CH2:59][CH:60]([CH3:62])[CH3:61])[NH2:58])([CH3:54])([CH3:53])[CH3:52]>CN(C=O)C.C(Cl)CCl>[C:51]([O:55][C:56](=[O:63])[C@@H:57]([NH:58][C:27]([C:18]1[CH:17]=[C:16]([O:15][CH2:14][C:13]([N:9]2[CH2:10][CH2:11][CH2:12][C@H:8]2[C:6](=[O:7])[NH:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[O:30])[N:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:19]=1)=[O:28])[CH2:59][CH:60]([CH3:61])[CH3:62])([CH3:54])([CH3:53])[CH3:52]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 12451443tert-butyl (2S)-2-amino-4-methylpentanoate hydrochlorideHCID 668546955-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 66855115HCID 66855115, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 250 mg 5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid in 4 ml DMF were added 124 mg HOAt, 174 mg EDC, 0.37 ml DIPEA and 136 mg leucine tert-butyl ester hydrochloride. After stirring for 12 h it was concentrated and the residue dissolved in dichloromethane. It was extracted with aqueous LiCl (4% w/w), aqueous NaHCO3 and 0.1 M HCl. The organic layer was dried over MgSO4 and concentrated to furnish the crude coupling product as colorless oil.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionIt was extracted with aqueous LiCl (4% w/w), aqueous NaHCO3 and 0.1 M HCl
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customto furnish the crude coupling product as colorless oil

Sources & evidence

ORD record
ord-87016519dd824f0bb1729e6d7cad2f3f
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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