Lithium Hydroxide → HCID 178522495, compound

HRID 1478635Notes

Reaction equation

HRID 1478635 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:8]([C:9](=[O:31])[NH:10][CH:11]([CH2:25][C:26]2[N:27]=[CH:28][NH:29][CH:30]=2)[C:12]([NH:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:18]=3[N:19]=2)=[O:13])[O:7]1)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[F:24][C:22]1[CH:21]=[CH: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])[CH2:25][C:26]3[N:27]=[CH:28][NH:29][CH:30]=3)[S:16][C:17]=2[CH:23]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178472533HCID 178472533, compound

Product 1

HCID 178522495HCID 178522495, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 18f (125 mg, 0.26 mmol); LiOH (6.2 mg, 0.26 mmol); THF/MeOH/H2O (1.5 mL: 1.0 mL: 0.5 mL); yielded 31b as a white solid (46 mg, 39.1%). 1H NMR (400 MHz, MeOD-d4): δ 11.88 (bs, 1H), 8.89-8.83 (dd, 1H, J=7.4 Hz, J=7.4 Hz); 7.91-7.89 (d, 1H, J=2.5 Hz); 7.78-7.72 (q, 1H); 7.56 (s, 1H); 7.30 (td, 1H, J=2.6 Hz); 6.85 (s, 1H); 4.81-4.76 (m, 1H): 3.76-3.74 (dd, 1H, J=1.68 Hz); 3.45-3.43 (dd, 1H, J=1.65 Hz); 3.11-3.00 (m, 2H). 13C NMR (DMSO-d6, 100 MHz): 171.13, 167.48, 165.83, 160.32, 158.21, 145.64, 135.40, 133.23, 122.17, 114.83, 108.74, 53.86, 53.40, 51.86. ESI-HRMS (m/z): [M+H+] calcd. for C17H14FN5O5S: 420.0773, observed: 420.0769.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-c8a3d443cfb147e0a3f0c5371978c786
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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