4-Methylmorpholine → HCID 11701865, compound

HRID 1158499Notes

Reaction equation

[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([OH:12])=O)[CH:7]([CH3:9])[CH3:8])=[O:4].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH2:41]([NH:48][NH2:49])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CCN(CC)CC>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([C:10]([NH:49][NH:48][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:12])[CH:7]([CH3:9])[CH3:8]

Participants

Reactant 6

HCID 79724-Methylmorpholine

HCID 8471Triethylamine

HCID 11157(Phenylmethyl)hydrazine

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

HCID 757711-Hydroxybenzotriazole

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 11701865HCID 11701865, compoundYield 65%

Procedure

The general procedure for the preparation of hydrazides described above was followed using N-(methoxycarbonyl)-(L)-valine (J. Med. Chem., 39, 3203-3216, 1996) (2.11 g, 12.0 mmol), EDAC (2.41 g, 12.6 mmol), HOBT (1.70 g, 12.6 mmol), NMM (1.38 mL, 12.6 mmol), benzylhydrazine×2HCl (2.45 g, 12.6 mmol) and Et3N (3.52 mL, 25.0 mmol), which gave the title compound (2.08 g, 65%) as a light yellow solid.

Sources & evidence

ORD record: ord-e805c36ded9649e69f113e2d260a92c7
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807677B2

Reaction notes

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