Triethylamine → (S)-alpha-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(pyrazol-1-yl)propionamide

関与物質

役割	名称	HCID	仕込み量
反応物	Triethylamine	HCID 8471	—
反応物	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
反応物	(S)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-pyrazol-1-YL)propanoic acid	HCID 11231563	—
反応物	(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol	HCID 14930738	—
溶媒	Acetonitrile	HCID 6342	—
生成物	(S)-alpha-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(pyrazol-1-yl)propionamide	HCID 53680317	—

反応手順

1.03 g (2.83 mmol) of HBTU and 0.39 ml (2.83 mmol) of triethylamine were added to a solution of 820 mg (2.83 mmol) of N-[(benzyloxy)carbonyl]-3-(pyrazol-1-yl)-L-alanine [J. Am. Chem. Soc. 107, 7105 (1985)]and 644 mg (2.83 mmol) of (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol in 28 ml of acetonitrile and the mixture was stirred at room temperature overnight. The crystals obtained after filtration were dissolved in 30 ml of ethanol and hydrogenated at 400 for two hours. Filtration over diatomaceous earth and evaporation under reduced pressure yielded 670 mg of (S)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(pyrazol-1-yl)propionamide, MS: 365 (M+H)+, as a colourless foam.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US05393875
出典データセット	uspto-grants-1995_02
ORD ID	ord-b34087caac06438a9d4b9820a61fbc61
出典メモ	uspto-grants-1995_02