Lithium Hydroxide → HCID 178522496, compound

HRID 1478634Notes

Reaction equation

HRID 1478634 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 178472534HCID 178472534, compound

Product 1

HCID 178522496HCID 178522496, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 18e (153 mg, 0.32 mmol); LiOH (7.7 mg, 0.32 mmol); THF/MeOH/H2O (3.5 mL: 1.5 mL: 1.5 mL); yielded 31a as a white solid (103 mg, 71.5%). 1H NMR (DMSO-d6, 400 MHz): δ 14.55 (bs, 1H); 14.36 (bs, 1H); 9.18-9.02 (m, 1H): 7.93-7.91 (m, 1H); 7.79-7.75 (m, 1H); 7.44 (s, 1H); 7.31-7.29 (t, 1H); 4.96-4.91 (q, 1H); 3.72-3.71 (d, 1H, J=1.62 Hz); 3.51-3.50 (d, 1H, J=1.62 Hz); 3.29-3.16 (m, 2H). %). 13C NMR (DMSO-d6, 100 MHz): 169.50, 168.51, 165.84, 165.84, 159.82, 157.53, 157.44, 145.02, 133.67, 132.68, 132.57, 128.56, 121.63, 117.01, 114.40, 114.16, 108.27, 108.00, 52.67, 52.19, 51.34, 26.20. ESI-HRMS (m/z): [M+H+] calcd. for C17H14FN5O5S: 420.0773, observed: 420.0777.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-dd5f16e31ddc4071ad292ec6ee2fab82
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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