Lithium Hydroxide → HCID 178521937, compound

HRID 1478631Notes

Reaction equation

HRID 1478631 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:27])[NH:10][C@@H:11]([CH2:21][C:22]2[NH:26][CH:25]=[N:24][CH:23]=2)[C:12](=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:7]1)=[O:5])C.[Li+].[OH-]>CO.O>[NH:24]1[CH:23]=[C:22]([CH2:21][C@H:11]([NH:10][C:9]([C@H:8]2[O:7][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:27])[C:12](=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:26]=[CH:25]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117857973HCID 117857973, compound

Product 1

HCID 178521937HCID 178521937, compoundYield 38.7%

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 18a (155 mg, 0.3 mmol); LiOH (14 mg, 0.58 mmol); MeOH/H2O (1.5 mL: 0.5 mL: 0.5 mL); yielded 28 as a white solid (40 mg, 27.1%). 1H NMR (MeOD-d4, 400 MHz): δ 8.66 (s, 1H); 7.57-7.55 (d, 2H, J=7.86 Hz); 7.29-7.27 (t, 3H); 7.10-7.07 (t, 1H); 4.97-4.94 (q, 1H); 3.64-3.63 (d, 1H, J=1.66 Hz); 3.529-3.525 (d, 1H, J=1.66 Hz); 3.36-3.15 (m, 2H). 13C NMR (MeOD-d4, 100 MHz): 169.79, 167.26, 166.95, 137.90, 134.99, 128.37, 124.10, 120.11, 54.13, 52.94, 51.67. ESI-HRMS (m/z): [M+H+] calcd. for C16H16N4O5: 345.1194, observed: 345.1185. HPLC Method 1: Rt=18.2 min, purity=95.2%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e53e655fd0b5433aa05c0e81603169cc
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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