HCID 533450, compound → HCID 86591128, compound

HRID 276706Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C@H:14]([C:19]([OH:21])=O)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12].[C:22]([CH:24]([NH2:35])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)#[N:23].C(C(NC(C(NC(C1C=CC2C(=CC=CC=2)C=1)=O)CC(C)C)=O)CC(C)C)#N>>[C:22]([CH:24]([NH:35][C:19]([CH:14]([NH:13][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12])[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:21])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)#[N:23]

Participants

Reactant 3

HCID 533450HCID 533450, compound

HCID 22951556HCID 22951556, compound

HCID 68440021HCID 68440021, compound

Product 1

HCID 86591128HCID 86591128, compoundYield 36%

Procedure

The title compound is prepared analogously to the compound of Example 22. N-(Naphthalene-2-carbonyl)-leucine and 1-cyano-2-(1H-indol-3-yl)-ethylamine (CAS 169545-97-5) are reacted by the same procedure as for Naphthalene-2-carboxylic acid [1-(1-cyano-3-methyl-butylcarbamoyl)-3-methyl-butyl]-amide, to give the product in 36% yield after chromatography on silica gel (hexane/ethyl acetate 1/1) (mixture of epimers).

Workup

customto give the product in 36% yield after chromatography on silica gel (hexane/ethyl acetate 1/1) (mixture of epimers)

Sources & evidence

ORD record: ord-33f75f7503f2430fb11692fda09dbeac
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353017B1

Reaction notes

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