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

HRID 1478656Notes

Reaction equation

HRID 1478656 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[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[CH:20]=2)=[O:13])[O:7]1)=[O:5])C.[Li+].[OH-]>>[C:22]1([CH3:29])[CH:23]=[C:24]([CH3:28])[CH:25]=[C:26]([CH3:27])[C:21]=1[N:19]1[CH:20]=[C:16]([CH2:15][NH:14][C:12](=[O:13])[C@@H:11]([NH:10][C:9]([C@H:8]2[O:7][C@@H:6]2[C:4]([OH:5])=[O:3])=[O:36])[CH2:30][C:31]2[N:32]=[CH:33][S:34][CH:35]=2)[N:17]=[N:18]1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 131736518(2S,3S)-ethyl-3-((S)-1-((1-mesityl-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Product 1

HCID 71818227(2S,3S)-3-((S)-1-((1-mesityl-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylic acidYield 66.1%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 47 (24 mg, 0.05 mmol); LiOH (1.1 mg, 0.05 mmol); after extraction afforded the desired product as a white solid (15 mg, 66.1%). 1H NMR (DMSO-d6, 400 MHz): δ 8.98-8.97 (d, 1H, J=1.87 Hz); 8.72-8.70 (t, 1H, J=11.2 Hz); 8.55-8.53 (d, 1H, J=8.23 Hz); 7.93 (s, 1H): 7.34 (s, 1H); 7.08 (s, 1H); 4.68-4.63 (m, 1H); 4.42-4.40 (d, 2H, J=5.50 Hz); 3.61-3.50 (m, 4H); 2.32 (s, 3H); 1.86 (s, 6H). 13C NMR (DMSO-d6, 100 MHz): 170.29, 165.60, 153.65, 152.98, 144.93, 139.46, 134.51, 133.50, 128.90, 124.69, 115.78, 52.79, 52.58, 48.66, 34, 54, 33.10, 20.69, 16.89. HRMS-ESI: m/z [M+H+] calculated for C22H24N6O5S: 485.5343, observed: m/z 485.1622 (M+H+): m/z 483.1600 (M−H+); HPLC Method 2: Rt=23.6 min; 97.4%.

Workup

  1. extractionafter extraction

Sources & evidence

ORD record
ord-021df1038ad44e7bae9c6a90827abab2
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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