4-Methylmorpholine → HCID 178434957, compound

HRID 535167Notes

Reaction equation

HRID 535167 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.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O[CH2:53][C:54]1[O:55][C:56](=[O:60])[O:57][C:58]=1[CH3:59].CN1CCOCC1>C(Cl)Cl.CC(O)=O>[CH3:59][C:58]1[O:57][C:56](=[O:60])[O:55][C:54]=1[CH2:53][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]1[NH:21][N:22]=[N:23][CH:24]=1)=[O:19])[CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:2][CH:3]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 105108784-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-oneHCID 178459153HCID 178459153, compound

Product 1

HCID 178434957HCID 178434957, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid (100 mg, 245 μmol, 1.0 eq.), EDCI (52 μL, 294 μmol, 1.2 eq.) and HOBt (39.7 mg, 294 μmol, 1.2 eq.) were dissolved in DCM (5 mL). After stirring for 10 minutes, 4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one (127 mg, 979 μmol, 4.0 eq.) was added. The mixture was stirred for 1 hour and 4-methylmorpholine (40.4 μL, 1.5 eq.) was added. After 1 hour, the crude material was dissolved in AcOH and purified by preparative HPLC to yield the title compound (20 mg). MS m/z [M+H]+ calc'd for C27H28N4O7, 521.20. found 521.4.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. waitAfter 1 hour
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-dd360fb3cacb4438b87c3df8cf9c431a
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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