Dimethylformamide → {(S)-1-[(S)-2-((2S,4S)-4-Amino-2-isopropylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/1481926

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Isopropylamine	HCID 6363	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	(2S,4S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid	HCID 90231415	—
Product	{(S)-1-[(S)-2-((2S,4S)-4-Amino-2-isopropylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester	HCID 90231470	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To (2S,4S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid (Intermediate 27) (50 mg, 73.9 μmol) in DMF at 0° C. was added DIPEA (29 mg, 222 mol) and HATU (31 mg, 81.3 μmol) and the mixture was stirred at 0° C. for 15 minutes. Isopropylamine (0.10 mL) was added, the cooling bath was removed and the mixture stirred at room temperature for 1 h. The mixture was evaporated to afford the title compound which was used without purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09409888B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-feba5b00fc9c40eca768e4b917ad65c3
Source note	uspto-grants-2016_08