4-Methylmorpholine → HCID 11543876, compound

HRID 1158500Notes

Reaction equation

[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[C:7]([CH3:10])([CH3:9])[CH3:8])=[O:4].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH2:42]([NH:49][NH2:50])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CCN(CC)CC>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([C:11]([NH:50][NH:49][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:13])[C:7]([CH3:10])([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 11263950N-(Methoxycarbonyl)-L-tert-leucine

Product 1

HCID 11543876HCID 11543876, compoundYield 50%

Procedure

The general procedure for the preparation of hydrazides described above was followed using N-(methoxycarbonyl)-(L)-tert-leucine (J. Med. Chem., 41, 3387-3401, 1998) (1.56 g, 8.24 mmol), EDAC (1.74 g, 9.08 mmol), HOBT (1.22 g, 9.03 mmol), NMM (0.995 mL, 9.05 mmol), benzylhydrazine×2HCl (1.61 g, 8.25 mmol) and Et3N (2.53 mL, 18.0 mmol) which gave the title compound (1.21 g, 50%) as a light yellow solid.

Sources & evidence

ORD record: ord-dfff7d80564c4ce18c4913b4273de971
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807677B2

Reaction notes

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