Lithium Hydroxide → Calpain inhibitor-1

Participants

Role	Name	HCID	Charge
Reactant	Lithium Hydroxide	HCID 3939	—
Reactant	(2S,3S)-ethyl-3-((S)-1-((1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate	HCID 117863624	—
Product	Calpain inhibitor-1	HCID 71660816	76.2%

Reaction Steps

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 39 (25 mg, 0.51 mmol); LiOH (1.3 mg, 0.06 mmol); after extraction afforded the desired product as a white solid (18 mg, 76.2%). 1H NMR (DMSO-d6, 400 MHz): δ 8.98 (s, 1H); 8.72-8.70 (t, 1H); 8.57-8.55 (d, 1H, J=8.06); 8.48 (s, 1H); 7.93-7.90 (q, 2H); 7.48-7.44 (t, 2H); 7.34 (s, 1H); 4.70-4.65 (q, 1H); 4.40-4.38 (d, 2H; J=5.52); 3.66 (s, 1H); 3.54-3.06 (m, 3H). 13C NMR (DMSO-d6, 100 MHz): 170.62, 165.75, 163.24, 160.80, 154.06, 153.32, 146.40, 133.62, 122.81, 122.72, 121.76, 117.33, 117.10, 53.24, 53.01, 52.94, 34.77, 33.50. HRMS-ESI: m/z [M+H+] calculated for C19H17FN6O5S: 461.1043, observed: m/z 461.1049 (M+H+): HPLC Method 2: Rt=17.9 min; purity=97.2%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403843B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-056f8cd4de4e4bd4a30c99fa9d66e772
Source note	uspto-grants-2016_08