Lithium Hydroxide → HCID 71817938, compound

HRID 1478639Notes

Reaction equation

HRID 1478639 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:34])[NH:10][C@@H:11]([CH2:27][C:28]2[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=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:34])[CH2:27][C:28]3[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=3)[S:16][CH:17]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71817632HCID 71817632, compound

Product 1

HCID 71817938HCID 71817938, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 20 (129 mg, 0.26 mmol): LiOH (6.3 mg, 0.26 mmol); THF/MeOH/H2O (2.5 mL: 1.5 mL: 1.5 mL); yielded 35 as a white solid (56 mg, 46.1%). 1H NMR (DMSO-d6, 400 MHz): 8.92-8.90 (d, 1H); 7.96-7.91 (m, 2H): 7.68 (s, 1H); 7.35-7.24 (m, 3H); 4.94-4.87 (m, 1H); 4.64-4.56 (m, 2H); 3.82-3.50 (m, 5H). 13C NMR (400 MHz, DMSO-d6): 171.52, 167.50, 165.57, 162.45, 161.02, 148.42, 138.62, 131.27, 128.18, 128.01, 127.83, 127.05, 116.17, 115.99, 106.70, 53.24, 52, 58, 51.90, 31.29, 29.52. ESI-HRMS (m/z): [M+H+] calcd. for C20H18FN5O5S: 460.1085; observed, 460.1092; Rt=17.8 min, purity=93.6%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-173775579fa84106a5cd69ab1fcfb7fa
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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