Lithium Hydroxide → Oxiranecarboxylic acid, 3-[[[1-[[[4-[[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-1-oxopentyl]amino]butyl]amino]carbonyl]-3-methylbutyl]amino]carbonyl]-, [3aS-[3aα,4β[R*(2R*,3R*)],6aα]]-

HRID 1478630Notes

Reaction equation

HRID 1478630 reaction equation
C([O:3][C:4]([C@@H:6]1[C@H:8]([C:9](=[O:39])[NH:10][C@@H:11]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:12](=[O:34])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:33])[CH2:20][CH2:21][CH2:22][CH2:23][C@H:24]2[C@@H:31]3[C@@H:27]([NH:28][C:29](=[O:32])[NH:30]3)[CH2:26][S:25]2)[O:7]1)=[O:5])C.[Li+].[OH-]>CO.O>[CH3:37][CH:36]([CH3:38])[CH2:35][C@H:11]([NH:10][C:9]([C@H:8]1[O:7][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:39])[C:12](=[O:34])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:33])[CH2:20][CH2:21][CH2:22][CH2:23][C@H:24]1[C@@H:31]2[C@@H:27]([NH:28][C:29](=[O:32])[NH:30]2)[CH2:26][S:25]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117857718HCID 117857718, compound

Product 1

HCID 71817786Oxiranecarboxylic acid, 3-[[[1-[[[4-[[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-1-oxopentyl]amino]butyl]amino]carbonyl]-3-methylbutyl]amino]carbonyl]-, [3aS-[3aα,4β[R*(2R*,3R*)],6aα]]-Yield 27.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Synthesized following general saponification procedure using the following quantities: the corresponding peptidomimetic epoxide ethyl ester 17h (155 mg, 0.3 mmol): LiOH (14 mg, 0.58 mmol); MeOH/H2O (1.5 mL: 0.5 mL: 0.5 mL); yielded 27 as a white solid (40 mg, 27.1%). 1H NMR (DMSO-d6, 400 MHz): 8.56 (d, 1H); 8.06 (t, 1H); 7.76 (t, 1H); 6.41 (s, 1H), 6.35 (s, 1H); 4.57 (m, 2H); 4.31 (m, 1H); 3.66 (d, 1H); 3.31 (d, 1H); 3.08 (m, 1H); 3.01 (m, 3H); 2.80 (dd, 1H); 2.56 (d, 1H); 2.04 (t, 2H); 1.53 (m, 6H); 1.43 (m, 3H); 1.36 (m, 2H); 0.89 (d, 3H); 0.84 (d, 3H). 13C NMR (DMSO-d6, 100 MHz): 171.80, 171.06, 568.78, 164.85, 162.68, 61.00, 59.16, 55.36, 52.65, 51.19, 41.14, 35.17, 28.17, 27.98, 26.59, 26.45, 25.28, 24.24, 22.87, 21.61. ESI-HRMS (m/z): no ionization, mass not seen. HPLC Method 1: Rt=14.8 min, purity=95.6%.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-690b60c222a34325933e685b28345b4e
Source dataset
uspto-grants-2016_08
Patent number
US09403843B2

Reaction notes

Loading…