Propylamine → HCID 71715115, compound

HRID 1477552Notes

Reaction equation

C[O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[OH:23])=[O:12])[CH2:7][N:6]1[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=O.[CH2:31]([NH2:34])[CH2:32][CH3:33].C[Al](C)C>>[CH2:31]([NH:34][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[OH:23])=[O:12])[CH2:7][N:6]1[CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)=[O:2])[CH2:32][CH3:33]

Participants

Reactant 3

HCID 7852Propylamine

HCID 16682925Trimethylaluminum

HCID 71715056HCID 71715056, compound

Product 1

HCID 71715115HCID 71715115, compoundYield 18.7%

Conditions

Temperature: 100 °C

Procedure

To a mixture of (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (150 mg, 0.37 mmol) and 44 mg of n-propyl amine was added Me3Al (catalytic amount, 2M in toluene) under an argon atmosphere in a seal tube and the mixture was heated at 100° C. for 16 hr. The reaction mixture was then quenched with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude was then purified by silica gel column chromatography to give (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid propylamide (30 mg, 18.7% yield) as a white solid. MS calcd. for C26H36N3O3 [(M+H)+] 438.0, obsd. 438.2.

Workup

customThe reaction mixture was then quenched with water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated
customThe crude was then purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9e39b055a0ec4fdbb2f38fec1f59f4cc
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403805B2

Reaction notes

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