Lithium Hydroxide → HCID 71818387, compound

HRID 1478626Notes

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 117857541HCID 117857541, compound

Product 1

HCID 71818387HCID 71818387, compoundYield 75.3%

Procedure

Followed general procedure using: the corresponding peptidomimetic epoxide ethyl ester 17c (85 mg, 0.22 mmol); LiOH (5.2 mg, 0.22 mmol); after extraction afforded the desired product as a white solid (59 mg, 74.8%). 1H NMR (DMSO-d6, 400 MHz): δ 9.88 (s, 1H); 8.81-8.79 (d, 1H, J=8.21 Hz); 7.38-7.33 (m, 1H); 7.17-7.13 (t, 2H); 4.61-4.56 (q, 1H); 3.70-3.69 (d, 1H, J=1.79 Hz); 3.52-3.51 (d, 1H, J=1.79 Hz); 1.66-1.58 (m, 3H); 0.93-0.88 (dd, 6H). 13C NMR (DMSO-d6, 100 MHz): 171.35, 169.20, 165.79, 159.48 (d, J=5.16 Hz); 157.01 (d, J=5.21 Hz); 128.58 (t, 19.7 Hz); 114.63 (t, J=34.0 Hz); 112.39 (d, J=22.6 Hz); 53.05, 51.71, 51.62, 41.32, 24.71, 21.96. ESI-HRMS (m/z): [M−H]+ calcd. for C16H20N2O5: 355.3216, observed: 355.3201. HPLC Method 1: Rt=18.9 min, purity=96.5%.

Workup

extractionafter extraction

Sources & evidence

ORD record: ord-260e0aafe648488e8872d75a74b53746
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403843B2

Reaction notes

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