4-Methylmorpholine → HCID 88011864, compound

HRID 2180235Notes

Reaction equation

HRID 2180235 reaction equation
C(OC([NH:8][C@H:9]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH:10]([OH:19])[C:11]([NH:13][O:14][CH2:15][C:16]([OH:18])=O)=[O:12])=O)(C)(C)C.Cl.[CH2:28]([O:30][C:31](=[O:35])[C@H:32]([CH3:34])[NH2:33])[CH3:29].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCl>[NH2:8][C@H:9]([CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[CH:10]([OH:19])[C:11]([NH:13][O:14][CH2:15][C:16]([NH:33][C@@H:32]([CH3:34])[C:31]([O:30][CH2:28][CH3:29])=[O:35])=[O:18])=[O:12]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 87999122HCID 87999122, compound

Product 1

HCID 88011864HCID 88011864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 118A (0.17 g, 0.45 mmol), L-alanine ethyl ester hydrochloride (0.098 g, 0.64 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.098 g, 0.51 mmol), 1-hydroxybenzotriazole (0.091 g, 0.67 mmol), and N-methylmorpholine (0.11 mL, 1.0 mmol) in dichloromethane (5 mL) at room temperature was stirred for 16 hours, diluted with dichloromethane, washed sequentially with 1 M HCl, aqueous NaHCO3, dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in saturated HCl/dioxane (4 mL), stirred for 1 hour, concentrated, then purified by HPLC to provide the desired product.

Workup

  1. washwashed sequentially with 1 M HCl, aqueous NaHCO3
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe concentrate was dissolved in saturated HCl/dioxane (4 mL)
  6. concentrationconcentrated
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-194cd4e2b96643f69b6b6f6c46dc164a
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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