Lithium Hydroxide → HCID 71679024, compound

HRID 1478640Notes

Reaction equation

HRID 1478640 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:29]=[CH:30][N:31]([CH3:33])[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:34])[CH2:27][C:28]3[N:29]=[CH:30][N:31]([CH3:33])[CH:32]=3)[S:16][CH:17]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71817633HCID 71817633, compound

Product 1

HCID 71679024HCID 71679024, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 21 (93 mg, 0.19 mmol); LiOH (4.5 mg, 0.19 mmol); THF/MeOH/H2O (1.5 mL: 0.5 mL: 0.5 mL); yielded 36 as a white solid (29 mg, 33.1%). 1H NMR (400 MHz, DMSO-d6): 12.50 (bs, 1H), 8.82-8.80 (d, 1H): 7.93-7.91 (m, 2H); 7.76 (s, 1H); 7.63 (s, 1H); 7.46-7.24 (t, 2H); 6.99 (s, 1H); 4.79-4.74 (m, 1H); 3.67-3.66 (d, 1H); 3.62 (s, 3H); 3.49-3.48 (d, 1H); 3.12-2.90 (m, 2H). 13C NMR (400 MHz, DMSO-d6): 169.72, 168.60, 165.56, 162.97, 160.54, 157.78, 147.88, 137.17, 130.84, 127.71, 127.63, 118.35, 115.68, 115.47, 108.08, 53.07, 52.98, 51.56, 33.11, 29.60. ESI-HRMS (m/z): [M+H+] calcd. for C20H18FNO5S: 460.1085, observed: 460.1090. Rt=18.1 min, purity=95.3%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-e39294658cac413088b0a68e3e2f020a
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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