Diisopropylethylamine → HCID 51968676, compound

HRID 2063474Notes

Reaction equation

HRID 2063474 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C@@H:21]([NH2:23])[CH3:22])=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C@@H:21]([NH:23][C:10]([C@H:9]2[CH2:13][CH2:14][CH2:15][N:8]2[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[O:12])[CH3:22])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 1550852(S)-(-)-1-(4-chlorophenyl)ethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 51968676HCID 51968676, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boc-D-Proline (4.3 g, 20 mmol) was dissolved in DMF (100 ml). Then (S)-4-Chloro-α-methybenzylamine (3 ml, 22 mmol) and HBTU (7.58 g, 20 mmol), DIEA (6.96 ml, 40 mmol) were added while stirring. The reaction mixture was stirred overnight. The reaction mixture was diluted with EtOAc (100 ml), washed with 1N HCl (2×50 ml), sat. aq. NaHCO3 (2×50 ml) and brine, dried over Na2SO4, and concentrated in vacuo. The crude desired product as a white solid (6 g, 85.7%) directly used for next step.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. washwashed with 1N HCl (2×50 ml), sat. aq. NaHCO3 (2×50 ml) and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-feb2f1caed594f49b8009c4e6e998c89
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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