Lithium Hydroxide → HCID 71817784, compound

HRID 1478629Notes

Reaction equation

HRID 1478629 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:34])[NH:10][C@@H:11]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[O:13])[O:7]1)=[O:5])C.[Li+].[OH-]>>[F:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:12](=[O:13])[C@@H:11]([NH:10][C:9]([C@H:8]2[O:7][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:34])[CH2:30][CH:31]([CH3:32])[CH3:33])(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 117857705HCID 117857705, compound

Product 1

HCID 71817784HCID 71817784, compoundYield 55.3%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17f (213 mg, 0.42 mmol); LiOH (21 mg, 0.85 mmol); after extraction afforded the desired product as a white solid (110 mg, 54.7%). 1H NMR (DMSO-d6, 400 MHz): δ 8.15 (s, 1H); 7.89-7.85 (m, 2H); 7.38 (s, 1H); 7.21-7.17 (t, 2H); 6.14 (s, 1H); 3.68-3.60 (d, 2H); 3.38-3.37 (d, 1H, J=1.60 Hz); 3.10-3.09 (d, 1H, J=1.60 Hz); 2.97 (s, 1H); 2.85 (s, 1H); 1.65-1.56 (m, 7H); 0.91-0.88 (m, 6H). 13C NMR (DMSO-d6, 100 MHz): 173.41, 170.47, 166.90, 166.52, 163.99, 135.75, 135.72, 130.03, 129.93, 116.71, 116.48, 53.83, 52.32, 43.08, 41.34, 39.65, 26.76, 26.22, 24.95, 22.94, 22.06. ESI-HRMS (m/z): [M+H+] calcd. for C20H28FN3O7S: 474.5705, observed: 474.5707. HPLC Method 1: Rt=20.9 min, purity=99.0%.

Workup

  1. extractionafter extraction

Sources & evidence

ORD record
ord-e9460230da0c4081b82425f4556c0c92
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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