Diisopropylethylamine → HCID 86644631, compound

HRID 1662070Notes

Reaction equation

HRID 1662070 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:14]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][C@@H:28]([C:42](O)=[O:43])[NH:29][C:30]([C:32]1[N:33]([CH3:41])[C:34]2[C:39]([CH:40]=1)=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>O.C(OCC)(=O)C.CN(C=O)C>[CH2:14]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][C@@H:28]([C:42]([NH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:43])[NH:29][C:30]([C:32]1[N:33]([CH3:41])[C:34]2[C:39]([CH:40]=1)=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

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 100126401071428-75-5HCID 68215386HCID 68215386, compound

Product 1

HCID 86644631HCID 86644631, compoundYield 73.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl (1R,2S)-2-aminocyclopentanecarboxylate (0.21 g), DMF (4.0 ml), and N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithine (0.40 g) were added HATU (0.40 g) and diisopropylethylamine (0.27 g) under ice-cooling, followed by stirring at room temperature for 11 hours. To the reaction mixture were added ethyl acetate and water under ice-cooling, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer was combined and washed with a 10% aqueous citric acid solution, a saturated sodium bicarbonate solution, water, and saturated brine in this order. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:THF=5:2→2:1) to obtain tert-butyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.41 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with a 10% aqueous citric acid solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:THF=5:2→2:1)

Sources & evidence

ORD record
ord-bdecd72383964f01b9df7efa833e1c84
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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