Diisopropylethylamine → HCID 130384719, compound

HRID 58814Notes

Reaction equation

HRID 58814 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[O:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]([NH:32][C@@H:33]([CH3:37])[C:34](O)=[O:35])=[O:31])[CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.CCOC(C)=O>[CH2:16]([O:15][C:10]1[CH:9]=[C:8]([CH2:7][C@H:2]([NH:1][C:34](=[O:35])[C@@H:33]([NH:32][C:30](=[O:31])[CH2:29][N:26]2[CH2:27][CH2:28][O:23][CH2:24][CH2:25]2)[CH3:37])[C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:12][C:11]=1[CH3:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=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 117607686(2-morpholinoacetyl)-L-alanineHCID 117690752(S)-methyl 2-amino-3-(3-(benzyloxy)-4-methylphenyl)propanoate

Product 1

HCID 130384719HCID 130384719, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude (S)-methyl 2-amino-3-(3-(benzyloxy)-4-methylphenyl)propanoate (TFA salt, 2.5 mmol) was dissolved in DMF (5 mL) and (S)-2-(2-morpholinoacetamido)propanoic acid (0.65 g, 3.0 mmol), HATU (1.43 g, 3.70 mmol), and DIEA (1.0 mL) were added at 0° C. with stirring. The reaction mixture was allowed to warm to ambient temperature and stirred for 3 h. EtOAc (100 mL) and water (100 mL) was added. The aqueous phase was extracted with EtOAc (30 mL×3) and the combined organic phases were washed with brine (50 mL×3), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (DCM/MeOH=20:1) to afford (S)-Methyl 3-(3-(benzyloxy)-4-methylphenyl)-2-((S)-2-(2-morpholinoacetamido) propanamido)propanoate (1.2 g, 96% yield).

Workup

  1. stirringstirred for 3 h
  2. extractionThe aqueous phase was extracted with EtOAc (30 mL×3)
  3. washthe combined organic phases were washed with brine (50 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel (DCM/MeOH=20:1)

Sources & evidence

ORD record
ord-87350e72512248b29572d2a57892b498
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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