Lithium Hydroxide → (2S,3S)-3-((S)-1-oxo-1-((1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylic acid

HRID 1478651Notes

Reaction equation

HRID 1478651 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:37])[NH:10][C@@H:11]([CH2:31][C:32]2[N:33]=[CH:34][S:35][CH:36]=2)[C:12](=[O:30])[NH:13][CH2:14][C:15]2[N:16]=[N:17][N:18]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:22][CH:21]=3)[CH:19]=2)[O:7]1)=[O:5])C.[Li+].[OH-]>>[O:30]=[C:12]([NH:13][CH2:14][C:15]1[N:16]=[N:17][N:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26](=[O:28])(=[O:29])[NH2:27])=[CH:22][CH:21]=2)[CH:19]=1)[C@@H:11]([NH:10][C:9]([C@H:8]1[O:7][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:37])[CH2:31][C:32]1[N:33]=[CH:34][S:35][CH:36]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 131736513(2S,3S)-ethyl-3-((S)-1-oxo-1-((1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Product 1

HCID 71818083(2S,3S)-3-((S)-1-oxo-1-((1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylic acidYield 45.1%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 42 (30 mg, 0.55 mmol); LiOH (1.3 mg, 0.055 mmol); product goes into aqueous layer during work up. Aqueous layer washed with CH2Cl2 and lyophilized to give the desired product as a white solid (8 mg, 45.1%). 1H NMR (DMSO-d6, 400 MHz): δ 9.00-8.99 (d, 1H, J=1.92 Hz); 8.79-8.76 (t, 1H); 8.70-8.68 (d, 1H, J=8.0 Hz); 8.66 (s, 1H); 8.12-8.01 (m, 4H); 7.55 (s, 2H); 7.36 (s, 1H); 4.70-4.65 (m, 1H); 4.41-4.40 (d, 2H, J=5.20 Hz); 3.61 (s, 1H); 3.44-3.10 (m, 3H). 13C NMR (DMSO-d6, 100 MHz): 372.25, 170.66, 169.06, 165.74, 154.10, 152.52, 138.29, 146.80, 144.19, 128.01, 121.75, 120.59, 116.29, 53.25, 52.98, 51.84, 49.01, 33.43. HRMS-ESI: m/z [M+H+] calculated for C19H19N7O7S2: 522.0865, observed: m/z 522.0858 (M+H+); HPLC method 2: Rt=14.8 min; purity=95.1%.

Workup

  1. washAqueous layer washed with CH2Cl2

Sources & evidence

ORD record
ord-c33642b95cc441a1ad7754420b891f0e
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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