4-Methylmorpholine → HCID 67717365, compound

HRID 2258453Notes

Reaction equation

HRID 2258453 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15](O)=[O:16])=[O:12])[C:4]=2[CH:3]=1.CN1C[CH2:29][O:28][CH2:27]C1.Cl.C[NH:33]OC>C1COCC1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15]([NH:33][CH2:29][O:28][CH3:27])=[O:16])=[O:12])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)2×HCID 108304472-[[(8-chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)carbonyl]amino]acetic acid

Product 1

HCID 67717365HCID 67717365, compoundYield 536.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the method described in Example 5, the title compound of Example 4 (1.2 g, 3.6 mmol) in 40 mL of THF was converted to its mixed anhydride with NMM (0.42 g, 3.6 mmol) and IBCF (0.49 g, 3.6 mmol) and coupled to N,O-dimethylhydroxylamine HCl (0.35 g, 3.6 mmol) using an additional 0.36 mmol (3.6 mmol) of NMM to liberate the free base of N,O-dimethylhydroxylamine HCl. This procedure gave 726 mg of the title compound after HPLC purification on silica gel.

Sources & evidence

ORD record
ord-b4459e72f10144c382b2b102edf099ab
Source dataset
uspto-grants-1997_08
Patent number
US05661146

Reaction notes

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