4-Methylmorpholine → [(1S)-1-(N'-Benzyl-hydrazinocarbonyl)-2,2-dimethyl-propyl]-carbamic acid benzyl ester

HRID 1158498Notes

Reaction equation

[C:1]([NH:11][C@H:12]([C:17]([OH:19])=O)[C:13]([CH3:16])([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH2:48]([NH:55][NH2:56])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.CCN(CC)CC>>[CH2:4]([O:3][C:1](=[O:2])[NH:11][C@H:12]([C:17]([NH:56][NH:55][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:19])[C:13]([CH3:14])([CH3:15])[CH3:16])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Reactant 6

HCID 79724-Methylmorpholine

HCID 8471Triethylamine

HCID 11157(Phenylmethyl)hydrazine

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

HCID 757711-Hydroxybenzotriazole

HCID 9899995(2S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 11639262[(1S)-1-(N'-Benzyl-hydrazinocarbonyl)-2,2-dimethyl-propyl]-carbamic acid benzyl esterYield 67%

Procedure

The general procedure for the preparation of hydrazides described above was followed using Cbz-(L)-tert-leucine (2.00 g, 4.48 mmol), EDAC (0.969 g, 5.05 mmol), HOBT (0.669 g, 4.95 mmol), NMM (0.542 mL, 4.93 mmol), benzylhydrazine×2HCl (0.962 g, 4.93 mmol) and Et3N (1.38 mL, 9.85 mmol) which gave the title compound (1.11 g, 67%) as a low melting solid.

Sources & evidence

ORD record: ord-f85c6b1f04f343e9bd427e0c46571b98
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807677B2

Reaction notes

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