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

HRID 1478654Notes

Reaction equation

HRID 1478654 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:36])[NH:10][C@@H:11]([CH2:30][C:31]2[N:32]=[CH:33][S:34][CH:35]=2)[C:12]([NH:14][CH2:15][C:16]2[N:17]=[N:18][N:19]([C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[CH:20]=2)=[O:13])[O:7]1)=[O:5])C.[Li+].[OH-]>>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([N:19]2[CH:20]=[C:16]([CH2:15][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:36])[CH2:30][C:31]3[N:32]=[CH:33][S:34][CH:35]=3)[N:17]=[N:18]2)=[CH:22][CH:23]=1)([O-:29])=[O:28]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 131736516(2S,3S)-ethyl-3-((S)-1-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Product 1

HCID 71818383(2S,3S)-3-((S)-1-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylic acidYield 82.1%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 45 (27 mg, 0.05 mmol); LiOH (1.2 mg, 0.05 mmol); after extraction afforded the desired product as a white solid (20 mg, 78.3%). 1H NMR (DMSO-d6, 400 MHz): δ 9.00-8.99 (d, 1H, J=1.79 Hz); 8.74-8.71 (t, 1H); 8.59 (s, 1H); 8.48-8.47 (d, 1H, J=8.42 Hz); 8.47-8.45 (d, 2H, J=9.15 Hz); 8.21-8.19 (d, 2H, J=9.15 Hz); 7.34-7.33 (d, 1H, J=1.78 Hz); 4.69-4.66 (q, 1H); 4.42-4.41 (d, 2H, J=5.60 Hz); 3.60-3.59 (d, 1H, J=1.79 Hz); 3.50-3.10 (m, 3H). 13C NMR (DMSO-d6, 100 MHz): 170.68, 169.07, 165.75, 154.10, 153.25, 147.11, 147.05, 141.26, 126.08, 121.95, 120.94, 116.23, 53.24, 52.95, 51.85, 34.69, 33.44. HRMS-ESI: m/z [M+H+] calculated for C19H17N7O7S: 488.4543, observed: m/z 488.0986 (M+H+); m/z 486.0864 (M−H+). HPLC Method 2: Rt=20.4 min; 93.4%.

Workup

  1. extractionafter extraction

Sources & evidence

ORD record
ord-b2fce8e7a7ca448ebb616344ced82de4
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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