Lithium Hydroxide → HCID 71679189, compound

HRID 1478625Notes

Reaction equation

C([O:3][C:4]([C@@H:6]1[C@@H:8]([C:9](=[O:27])[NH:10][C@@H:11]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]([NH:14][C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=2[F:22])=[O:13])[O:7]1)=[O:5])C.[Li+].[OH-]>>[F:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[NH:14][C:12](=[O:13])[C@@H:11]([NH:10][C:9]([C@H:8]1[O:7][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 117857838HCID 117857838, compound

Product 1

HCID 71679189HCID 71679189, compoundYield 77%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17b (28 mg, 0.72 mmol); LiOH (1.7 mg, 0.072 mmol); after extraction afforded the desired product as a white solid (20 mg, 77.0%). 1H NMR (MeOD-d4, 400 MHz): δ 7.91 (s, 1H); 7.36-7.31 (m, 1H); 7.07-7.02 (t, 2H); 4.72 (m, 1H); 3.65 (s, 1H); 3.52 (s, 1H); 1.74-1.68 (m, 3H); 1.01-0.99 (d, 6H). 13C NMR (DMSO-d6, 100 MHz): 171.26, 169.20, 165.81, 159.49 (d, J=5.2 Hz), 157.00 (d, J=5.2 Hz), 128.98 (t, J=19.7 Hz); 115.34 (t, J=34.0 Hz); 113.10 (d, J=5.2 Hz), 107.43, 106.22, 52.96, 51.51, 51.32, 41.30, 24.71, 23.81. ESI-HRMS (m/z): [M−H]+ calcd, for C16H20N2O5: 355.3216, observed: 355.3101. HPLC Method 1: Rt=19.7 min, purity=95.0%.

Workup

extractionafter extraction

Sources & evidence

ORD record: ord-4240cb69839b40cf953ef429ff20f0bc
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403843B2

Reaction notes

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