Lithium Hydroxide → HCID 71817937, compound

HRID 1478637Notes

Reaction equation

HRID 1478637 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:33])[NH:10][C@@H:11]([CH2:27][C:28]2[N:29]=[CH:30][S:31][CH:32]=2)[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-]>C1COCC1.CO.O>[F:26][C:23]1[CH:22]=[CH:21][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:33])[CH2:27][C:28]3[N:29]=[CH:30][S:31][CH:32]=3)[S:16][CH:17]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117857859HCID 117857859, compound

Product 1

HCID 71817937HCID 71817937, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 19b (974 mg, 2.0 mmol); LiOH (47.5 mg, 2.0 mmol); THF/MeOH/H2O (25 mL: 5 mL: 2 mL); yielded 33 as a white solid (685 mg, 74.6%). 1H NMR (MeOD-d4, 400 MHz): δ 8.99-8.98 (d, 1H, J=1.67 Hz); 7.94-7.91 (q, 2H); 7.37 (s, 1H); 7.36 (s, 1H); 7.15-7.10 (t, 2H); 5.06-5.02 (q, 1H); 3.64-3.63 (d, 1H, J=1.57 Hz): 3.49-3.45 (m, 3H). 13C NMR (MeOD-d4, 100 MHz): 170.05, 169.01, 166.19, 163.43, 158.19, 154.25, 152.66, 148.36, 131.30, 128.18, 116.63, 116.15, 115.93, 108.62, 53.12, 53.05, 52.21, 33.09. ESI-HRMS (m/z): [M+H+] calcd. for C19H15FN4O5S2: 463.0541, observed: 463.0545; HPLC method 2: Rt=23.3 min; purity=96.3%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-34f4f6ef770a406ea813d520a069121b
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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