Dimethylformamide → N-benzyloxy-N-[(R)-2-(N'-pyridin-2-yl-hydrazinocarbonyl)-heptyl]-formamide

HRID 2074973Notes

Reaction equation

[CH2:1]([O:8]C(NC[C@@H](CCCCC)C(O)=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1[CH:27]=[N:26][C:25]2[N:28](O)[N:29]=N[C:24]=2[CH:23]=1.N1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1NN.CN1[CH2:46][CH2:45][O:44]CC1.CCN=C=NCCCN(C)C.[CH3:58][N:59]([CH:61]=[O:62])C>>[CH2:1]([O:8][N:59]([CH2:58][C@H:46]([C:45]([NH:29][NH:28][C:25]1[CH:24]=[CH:23][CH:22]=[CH:27][N:26]=1)=[O:44])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:61]=[O:62])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 6

HCID 6228Dimethylformamide

HCID 79724-Methylmorpholine

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

HCID 786452-Hydrazinopyridine

HCID 181649HOAt

HCID 66603339(2R)-[(benzyloxyformylamino)methyl]heptanoic acid

Product 1

HCID 86600960N-benzyloxy-N-[(R)-2-(N'-pyridin-2-yl-hydrazinocarbonyl)-heptyl]-formamide

Procedure

(2R)-[(benzyloxyformylamino)methyl]heptanoic acid (1.2 mmoles), HOAt (1.3 mmoles), N′-pyridin-2-yl-hydrazine (1.2 mmoles) and NMM (5 mmoles) were dissolved in DMF and treated with EDCI (1.3 mmoles) at room temperature for 12 hours. The coupling product N-benzyloxy-N-[(R)-2-(N′-pyridin-2-yl-hydrazinocarbonyl)-heptyl]-formamide was isolated by prep hplc of the crude reaction mixture. This compound was submitted to atmospheric pressure hydrogenation over Pd/C in methanol for 1 hour, yielding the title compound. MH+295.

Sources & evidence

ORD record: ord-61d1cb24bf49496bb5340013bea9c567
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919528B2

Reaction notes

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