Lithium Hydroxide → HCID 178522535, compound

HRID 1478633Notes

Reaction equation

HRID 1478633 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:8]([C:9](=[O:33])[NH:10][CH:11]([CH2:27][C:28]2[N:29]=[CH:30][NH: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][NH:31][CH:32]=3)[S:16][CH:17]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178472535HCID 178472535, compound

Product 1

HCID 178522535HCID 178522535, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 18d (200 mg, 0.42 mmol); LiOH (12 mg, 0.50 mmol); THF/MeOH/H2O (2.5 mL: 1.5 mL: 1.5 mL); yielded 30b as a white solid (85 mg, 45.2%). 1H NMR (DMSO-d6, 400 MHz): δ 12.52 (bs, 1H); 8.85-8.75 (dd, 2H, J=6.9 Hz; J=43.1 Hz); 7.94-7.91 (t, 2H); 7.80 (s, 1H); 7.62 (s, 1H); 7.28-7.24 (t, 2H); 6.93 (s, 1H): 4.80-4.76 (q, 1H); 3.65-3.64 (d, 1H, J=4.40 Hz); 3.46-3.42 (d, 1H, J=14.0 Hz); 3.09-2.96 (m, 2H). 13C NMR (DMSO-d6, 100 MHz): 169.5, 168.8, 165.9, 162.9, 160.5, 157.6, 147.8, 134.6, 132.1, 130.7, 127.6, 116.4, 115.5 (d, J=21.4 Hz), 108.0, 52.9, 52.7, 52.6, 51.9, 28.6. ESI-HRMS (m/z): [M+H+] calcd. for C19H16FN5O5S: 446.0928, observed: 446.0939; HPLC method 2: Rt=15.8 min, purity=97.2%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e881c23609f2447098d7980630f830ec
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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