Diisopropylethylamine → HCID 57893125, compound

HRID 1511467Notes

Reaction equation

HRID 1511467 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:12][CH:13]1[CH2:15][CH2:14]1)[CH:4]([OH:11])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[C:16]([O:20][C:21]([N:23]1[CH2:27][C@H:26]([O:28][C:29]2[C:38]3[C:33](=[CH:34][C:35]([O:39][CH2:40][CH3:41])=[CH:36][CH:37]=3)[CH:32]=[CH:31][N:30]=2)[CH2:25][C@H:24]1[C:42](O)=[O:43])=[O:22])([CH3:19])([CH3:18])[CH3:17].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C)C=O.C(OCC)(=O)C>[C:16]([O:20][C:21]([N:23]1[CH2:27][C@H:26]([O:28][C:29]2[C:38]3[C:33](=[CH:34][C:35]([O:39][CH2:40][CH3:41])=[CH:36][CH:37]=3)[CH:32]=[CH:31][N:30]=2)[CH2:25][C@H:24]1[C:42](=[O:43])[NH:2][C@H:3]([CH:4]([OH:11])[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6])[CH2:12][CH:13]1[CH2:15][CH2:14]1)=[O:22])([CH3:18])([CH3:19])[CH3:17]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57893081HCID 57893081, compoundHCID 68913254HCID 68913254, compound

Product 1

HCID 57893125HCID 57893125, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To (3S)-3-amino-N,4-dicyclopropyl-2-hydroxybutanamide HCl salt (66 mgs, 0.28 mmol) in dichloromethane/N,N-dimethylformamide (10:3, 13 mL) was added (2S,4R)-1-(tert-butoxycarbonyl)-4-(6-ethoxyisoquinolin-1-yloxy)pyrrolidine-2-carboxylic acid (114 mgs, 0.28 mmol), O (7 azabenzotriazol 1 yl) 1,1,3,3 tetramethyl-uronium hexafluorophosphate (HATU) (128 mg, 0.34 mmol) and diisopropylethylamine (0.15 mL, 0.84 mmol). After 1 hour at room temperature, the reaction mixture was diluted with ethyl acetate and washed with 1N HCl (2×), sodium bicarbonate (1×), and brine (1×). The ethyl acetate layer was dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure to give (2S,4R)-tert-butyl-2-((2S)-1-cyclopropyl-4-(cyclopropylamino)-3-hydroxy-4-oxobutan-2-ylcarbamoyl)-4-(6-ethoxy-isoquinolin-1-yloxy)pyrrolidine-1-carboxylate.

Workup

  1. washwashed with 1N HCl (2×), sodium bicarbonate (1×), and brine (1×)
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c048a89c4ec24199964c9beb1d80067b
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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