4-Methylmorpholine → HCID 86599730, compound

HRID 643058Notes

Reaction equation

CCN=C=NCCCN(C)C.[CH:12]1[CH:13]=CC2N(O)N=N[C:16]=2[CH:17]=1.C[N:23]1[CH2:28][CH2:27][O:26]CC1.[C:29]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:32])[NH:30][NH2:31].[C:38]([O:41][CH2:42]C)(=[O:40])C>>[CH3:42][O:41][C:38]([NH:23][C@@H:28]([C@@H:12]([CH3:13])[CH2:17][CH3:16])[C:27]([NH:31][NH:30][C:29]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:26])=[O:40]

Participants

Reactant 5

HCID 79724-Methylmorpholine

HCID 8857Ethyl Acetate

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HCID 70091tert-Butyl carbazate

HCID 757711-Hydroxybenzotriazole

Product 1

HCID 86599730HCID 86599730, compoundYield 89%

Procedure

Example 3A (0.54 g, 2.85 mmol) was dissolved in ethyl acetate (14 mL) and treated with EDAC (0.49 g, 1.1 equivalents), HOBT (0.42 g, 1.1 equivalents), NMM (0.48 mL, 1.2 equivalents), and t-butyl carbazate (0.45 g, 1.2 equivalents) at 25° C. for 16 hrs. The mixture was washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered and the solvents were evaporated. The crude residue was purified using dichloromethane-7% methanol/dichloromethane to give 0.77 g (89%) of the title compound.

Workup

washThe mixture was washed with saturated sodium bicarbonate, water, brine
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvents were evaporated
customThe crude residue was purified

Sources & evidence

ORD record: ord-3e3c41c5148b4a86bb63ac87d7bf18c7
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696226B2

Reaction notes

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