Lithium Hydroxide → HCID 71817935, compound

HRID 1478632Notes

Reaction equation

HRID 1478632 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:30])[NH:10][C@@H:11]([CH2:24][C:25]2[NH:29][CH:28]=[N:27][CH:26]=2)[C:12]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[O:13])[O:7]1)=[O:5])C.[Li+].[OH-]>CO.O>[NH:29]1[C:25]([CH2:24][C@H:11]([NH:10][C:9]([C@H:8]2[O:7][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:30])[C:12]([NH:14][C:15]2[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=2[CH3:21])=[O:13])=[CH:26][N:27]=[CH:28]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117858103HCID 117858103, compound

Product 1

HCID 71817935HCID 71817935, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 18b (51.6 mg, 0.1 mmol); LiOH (5 mg, 0.2 mmol); MeOH/H2O (1.5 mL: 0.5 mL: 0.5 mL): yielded 29 as a white solid (26.2 mg, 54.2%). 1H NMR (MeOD-d4, 400 MHz): δ 7.62 (s. 1H); 6.93 (s, 1H); 6.87 (s, 2H); 4.84-4.82 (m, 1H); 3.53-3.49 (d, 1H); 3.38-3.35 (d, 1H); 3.25-3.22 (m, 2H); 2.25 (s, 3H); 2.07 (s, 6H). 13C NMR (MeOD-d4, 100 MHz): 174.40, 172.62, 170.80, 168.89, 136.54, 135.74, 135.11, 133.43, 131.25, 128.18, 117.26, 54.20, 53.82, 53.69, 52.80, 29.34, 19.55, 16.86. ESI-HRMS (m/z): [M−H+] calcd. for C19H22N4O5: 385.1517, observed: 385.1516. HPLC Method 2: Rt=16.4 min, purity=95.4%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-7328e67282a642dab6b5269fadd67cc9
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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