4-Methylmorpholine → HCID 130394597, compound

HRID 58817Notes

Reaction equation

HRID 58817 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.[NH2:12][C@@H:13]([CH3:37])[C:14]([NH:16][C@@H:17]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>ClCCl.O>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]([NH:12][C@@H:13]([CH3:37])[C:14]([NH:16][C@@H:17]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:15])=[O:11])[CH2:6][CH2:7]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 112059272-(4-Hydroxypiperidin-1-yl)acetic acidHCID 130394596(S)-benzyl 2-((S)-2-aminopropanamido)-3-(4-methoxyphenyl)propanoate

Product 1

HCID 130394597HCID 130394597, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-hydroxypiperidin-1-yl)acetic acid (0.41 g, 2.6 mmol) and (S)-benzyl 2-((S)-2-aminopropanamido)-3-(4-methoxyphenyl)propanoate (HCl salt, 0.93 g, 2.6 mmol) in dichloromethane (30 mL) at 0° C. was added HATU (1.1 g, 2.9 mmol) followed by N-methylmorpholine (1.05 g, 10.4 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. Water (30 mL) was added and the resulting mixture was extracted with dichloromethane (30 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 (petroleum ether/dichloromethane=5:1 to 1:1) to afford (S)-benzyl 2-((S)-2-(2-(4-hydroxypiperidin-1-yl)acetamido)propanamido)-3-(4-methoxyphenyl)propanoate (1.1 g, 87% yield) as a colorless solid.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane (30 mL×3)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/dichloromethane=5:1 to 1:1)

Sources & evidence

ORD record
ord-bee3b889c20c4fd0926f4ca805d1d0a7
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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