4-Methylmorpholine → HCID 178459154, compound

HRID 535179Notes

Reaction equation

HRID 535179 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:17][C:18]([C:20]2[NH:21][N:22]=[N:23][CH:24]=2)=[O:19])[CH2:9][C@:10]([CH2:15][OH:16])([CH3:14])[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:52]1[C:60]2[C:55](=[CH:56][C:57](O)=[CH:58][CH:59]=2)[CH2:54][CH2:53]1.CN1CCOCC1>C(Cl)Cl>[CH2:52]1[C:60]2[C:55](=[CH:56][C:57]([O:12][C:11](=[O:13])[C@@:10]([CH2:15][OH:16])([CH3:14])[CH2:9][C@H:8]([NH:17][C:18]([C:20]3[NH:21][N:22]=[N:23][CH:24]=3)=[O:19])[CH2:7][C:4]3[CH:5]=[CH:6][C:1]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:2][CH:3]=3)=[CH:58][CH:59]=2)[CH2:54][CH2:53]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 151185-IndanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178459153HCID 178459153, compound

Product 1

HCID 178459154HCID 178459154, compoundYield 0.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid (118 mg, 290 μmol), HOBt (118 mg, 871 μmol), and EDCI (154 μL, 871 μmol) were dissolved into DCM and stirred for 15 minutes. 5-Indanol (310 mg, 2.3 mmol) and 4-methylmorpholine (128 μL, 1.2 mmol) were added and the resulting mixture was stirred at room temperature for 2 hours. The reaction was quenched with water and the DCM layer was separated and concentrated. AcOH was added and the product was purified by preparative HPLC to yield the title compound (1.4 mg; purity 95%). MS m/z [M+H]+ calc'd for C31H32N4O4, 525.24. found 5254.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. customThe reaction was quenched with water
  3. customthe DCM layer was separated
  4. concentrationconcentrated
  5. additionAcOH was added
  6. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-29238923cdb04204af314fd93e75e43f
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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