4-Methylmorpholine → HCID 130394526, compound

HRID 58794Notes

Reaction equation

HRID 58794 reaction equation
CN1CCOCC1.[O:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:17][C@@H:18]([CH3:22])[C:19]([OH:21])=O)=[O:16])[CH2:10][CH2:9]1.[NH2:23][C@@H:24]([CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.O>[O:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]([NH:17][C@@H:18]([CH3:22])[C:19]([NH:23][C@@H:24]([CH2:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[O:21])=[O:16])[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15630398(S)-Benzyl 2-amino-4-phenylbutanoateHCID 117607686(2-morpholinoacetyl)-L-alanine

Product 1

HCID 130394526HCID 130394526, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-Methylmorpholine (1.09 g, 10.8 mmol) was added to a mixture of (S)-2-(2-morpholinoacetamido)propanoic acid (0.58 g, 2.7 mmol), (S)-benzyl 2-amino-4-phenylbutanoate (TFA salt, 1.03 g, 2.7 mmol) and HATU (1.13 g, 2.97 mmol) in dichloromethane (50 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. Water (50 mL) was added and the resulting mixture was extracted with dichloromethane (50 mL×3). The organic extracts were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=100:1 to 10:1) to afford (S)-benzyl 2-((S)-2-(2-morpholinoacetamido)propanamido)-4-phenylbutanoate (0.9 g, 71% yield).

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane (50 mL×3)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=100:1 to 10:1)

Sources & evidence

ORD record
ord-71cea4276bc04108ad0f3beef27ed796
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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