Lithium Hydroxide → HCID 71817783, compound

HRID 1478624Notes

Reaction equation

C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:25])[NH:10][C@@H:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12](=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:7]1)=[O:5])C.[Li+].[OH-]>>[CH3:23][CH:22]([CH3:24])[CH2:21][C@H:11]([NH:10][C:9]([C@H:8]1[O:7][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:25])[C:12](=[O:20])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 117857448HCID 117857448, compound

Product 1

HCID 71817783HCID 71817783, compoundYield 84.3%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17a (70 mg, 0.2 mmol); LiOH (4.8 mg, 0.2 mmol); after extraction afforded the desired product as a white solid (54 mg, 83.9%). 1H NMR (MeOD-d4, 400 MHz): δ 7.57-7.55 (d, 2H); 7.33-7.29 (t, 2H); 7.13-7.09 (t, 1H); 4.64-4.61 (m, 1H); 3.71 (s, 1H); 3.57 (s, 1H); 1.76-1.65 (m, 3H); 1.02-0.98 (t, 6H). 13C NMR (MeOD-d4, 100 MHz): 171.22, 169.07, 167.14, 137.98, 128.41, 124.12, 120.14, 52.90, 52.58, 51.69, 40.70, 29.49, 24.64, 22.04, 20.59. ESI-HRMS (m/z): [M−H]+ calcd. for C16H20N2O5: 319.3404, observed: 319.1332. HPLC Method 3: Rt=21.0 min, purity=96.1%.

Workup

extractionafter extraction

Sources & evidence

ORD record: ord-1127d3cd297f42608d651bc213ad3368
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403843B2

Reaction notes

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