4-Methylmorpholine → HCID 86632571, compound

HRID 660521Notes

Reaction equation

HRID 660521 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN[O:18][CH3:19].[CH3:20][N:21]1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([C:10](=[O:12])[NH:21][CH2:20][O:18][CH3:19])([CH3:14])[CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 86632571HCID 86632571, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-tert-butoxycarbonylamino-2-methyl-propionic acid (8.0 g, 39 mmol) and N,O-dimethylhydroxylamine hydrochloride (4.6 g, 47 mmol) in methylene chloride (80 mL) is added N-methylmorpholine (5.2 mL, 47 mmol), HOBT (6.4 g, 47 mmol) and EDCl (9.1 g, 47 mmol). The mixture is stirred at RT for 18 h then is washed sequentially with 10% citric acid (2×), sat. NaHCO3 (2×) and brine. The organic solution is dried over magnesium sulfate and the solvent removed under reduced pressure. The resulting oil is purified by flash chromatography to give the title compound.

Workup

  1. washthen is washed sequentially with 10% citric acid (2×), sat. NaHCO3 (2×) and brine
  2. dry with materialThe organic solution is dried over magnesium sulfate
  3. customthe solvent removed under reduced pressure
  4. customThe resulting oil is purified by flash chromatography

Sources & evidence

ORD record
ord-6bdcf4b66bee4cd88e5f822111ad4440
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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