Lithium Hydroxide → HCID 71679021, compound

HRID 1478627Notes

Reaction equation

HRID 1478627 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:31])[NH:10][C@@H:11]([CH2:27][CH:28]([CH3:30])[CH3:29])[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-]>>[F:26][C:23]1[CH:24]=[CH:25][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:31])[CH2:27][CH:28]([CH3:29])[CH3:30])[S:16][CH:17]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 71818230HCID 71818230, compound

Product 1

HCID 71679021HCID 71679021, compoundYield 79.1%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17d (203 mg, 0.45 mmol); LiOH (10.8 mg, 0.45 mmol); after extraction afforded the desired product as a white solid (150 mg, 78.8%). 1H NMR (DMSO-d6, 400 MHz): δ 12.51 (bs, 1H); 8.64-8.61 (d, 1H, J=12.0 Hz); 7.95-7.92 (t, 2H); 7.62 (s, 1H); 7.28-7.24 (t, 2H); 4.63-4.58 (m, 1H); 3.51-3.50 (d, 1H, J=1.60 Hz); 3.34-3.33 (d, 1H, J=1.60 Hz); 165-1.54 (m, 3H); 0.91-0.88 (t, 6H). 13C NMR (MeOD-d4, 100 MHz): 172.44, 165.32, 162.87, 159.37, 150.45, 132.60, 132.57, 129.14, 129.06, 116.56, 116.34, 108.69, 54.41, 53.55, 53.19, 41.79, 26.21, 23.54, 22.02. ESI-HRMS (m/z): [M+H+] calcd. for C19H20FN3O5S: 422.1180, observed: 422.1188. HPLC Method 1: Rt=24.6 min, purity=95.7%.

Workup

  1. extractionafter extraction

Sources & evidence

ORD record
ord-370c6574f5504b5fa8ae13a86e147194
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

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