Diisopropylethylamine → HCID 131735609, compound

HRID 528687Notes

Reaction equation

HRID 528687 reaction equation
CCN(C(C)C)C(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.[NH:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]#[N:27].[C:28]([O:32][C:33]([NH:35][C@H:36]([CH3:40])[C:37](O)=[O:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CN(C=O)C>[C:26]([C@@H:22]1[CH2:23][CH2:24][CH2:25][N:21]1[C:37](=[O:38])[C@H:36]([NH:35][C:33](=[O:34])[O:32][C:28]([CH3:30])([CH3:29])[CH3:31])[CH3:40])#[N:27]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 87797239(2S)-Pyrrolidine-2-carbonitrile p-toluene sulfonate

Product 1

HCID 131735609HCID 131735609, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of DIPEA (1,145 ml, 6.55 mmol) and (S)-pyrrolidine-2-carbonitrile 4-methylbenzenesulfonate (0.567 g, 2,114 mmol) in DCM was added to a mixture of (R)-2-(tert-butoxycarbonylamino)propanoic acid (0.4 g, 2.114 mmol) and HATU (0.804 g, 2.114 mmol) in DMF. After 3 h the mixture was washed with 1N citric acid and saturated sodium bicarbonate and brine. The organic layer was dried sodium sulfate, filtered and purified by column chromatography with a gradient DCM to DCM-MeOH (95-5). (0.47 g, 83%)

Workup

  1. washAfter 3 h the mixture was washed with 1N citric acid and saturated sodium bicarbonate and brine
  2. filtrationfiltered
  3. custompurified by column chromatography with a gradient DCM to DCM-MeOH (95-5)

Sources & evidence

ORD record
ord-c04bb06f62d0420b91af4b94c2a92520
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

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