Lithium Hydroxide → HCID 71679190, compound

HRID 1478628Notes

Reaction equation

C([O:3][C:4]([C@H:6]1[C@H:8]([C:9](=[O:31])[NH:10][C@@H:11]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:12]([NH:14][C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:19]=2)=[O:13])[O:7]1)=[O:5])C.[Li+].[OH-]>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]2[N:19]=[C:15]([NH:14][C:12](=[O:13])[C@@H:11]([NH:10][C:9]([C@@H:8]3[O:7][C@H:6]3[C:4]([OH:5])=[O:3])=[O:31])[CH2:27][CH:28]([CH3:29])[CH3:30])[S:16][CH:17]=2)=[CH:21][CH:22]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 71818231HCID 71818231, compound

Product 1

HCID 71679190HCID 71679190, compoundYield 75.6%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17e (76.4 mg, 0.16 mmol); LiOH (8 mg, 0.34 mmol); after extraction afforded the desired product as a white solid (51 mg, 71.5%). 1H NMR (DMSO-d6, 400 MHz): δ 12.52 (s, 1H); 8.78-8.76 (d, 1H, J=8.0 Hz); 7.94-7.92 (t, 2H); 7.63 (s, 1H); 7.29-7.24 (t, 2H); 4.58-4.57 (m, 1H); 3.62-3.61 (d, 1H, J=1.80 Hz); 3.41-3.40 (d, 1H, J=1.80 Hz); 1.64-1.51 (m, 3H): 0.91-0.88 (dd, 6H). 13C NMR (DMSO-d6, 100 MHz): 171.02, 166.26, 162.88, 160.46, 157.72, 147.81, 130.80, 130.77, 127.62, 127.54, 115.59 (d, J=21.6 Hz); 107.97, 52.36, 52.08, 51.37, 28.89, 24.25, 22.82, 21.19. EST-HRMS (m/z): [M+H+] calcd for C19H20FN3O5S: 422.1180, observed: 422.1186. HPLC Method 1: Rt=23.8 min, purity=95.1%.

Workup

extractionafter extraction

Sources & evidence

ORD record: ord-8fc013700c0a400a86c218487a8b4e16
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403843B2

Reaction notes

Loading…