1,2-Dichloroethane → N-[1(R)-[(3,4-dihydro-6-methyl-4-oxospiro[2H-1-benzopyran-2,4'-piperidin]-1'-yl)carbonyl]-2-(indol-3-yl)ethyl]-2-[[(1,1-dimethylethyloxy)carbonyl]amino]-2-methylpropanamide

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid	HCID 15895387	—
Reactant	6-Methylspiro[chroman-2,4'-piperidin]-4-one hydrochloride	HCID 19030425	—
Product	N-[1(R)-[(3,4-dihydro-6-methyl-4-oxospiro[2H-1-benzopyran-2,4'-piperidin]-1'-yl)carbonyl]-2-(indol-3-yl)ethyl]-2-[[(1,1-dimethylethyloxy)carbonyl]amino]-2-methylpropanamide	HCID 22862457	—

Reaction Steps

Prepared by the procedure described in Example 3, Step B. 3,4-Dihydro-6-methylspiro[2H- 1 -benzopyran-2,4'-piperidine]-4-one hydrochloride (20 mg, 0.058 mmol), (Hashigaki et al Chem. Pharm. Bull. 32 pg 3561-3568 (1984)) α(R)-[[2-[[(1,1-dimethylethoxy)-carbonyl]amino]-2,2-dimethyl-1-oxoethyl]amino]-1H-indole-3propanoic acid) (32 mg, 0.082 mmol), HOBT (1 eq.), N-methyl morpholine (0.03 mL, 0.28 mmol), and EDC (40 mg, 0.21 mmol). Reaction time: 8 hours. Yield: 34 mg (86%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05536716
Source dataset	uspto-grants-1996_07
ORD ID	ord-8203d1fbffa3418abd917e88eda9e3ed
Source note	uspto-grants-1996_07