Sodium Hydroxide → HCID 15940506, compound

HRID 2360647Notes

Reaction equation

HRID 2360647 reaction equation
C1([O:6][C:7](=[O:40])[C@@H:8]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28](=[O:39])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35](=[O:38])[NH:36][OH:37])[CH:22]=2)=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)CCCC1.[OH-].[Na+]>C1COCC1>[OH:37][NH:36][C:35]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:28]([NH:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][O:19][C:17]([NH:16][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]([OH:40])=[O:6])=[O:18])=[O:39])=[O:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15940366HCID 15940366, compound

Product 1

HCID 15940506HCID 15940506, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound (94) (100 mg, 0.18 mmol) was dissolved in THF (1 ml) and 2M NaOH (1 ml) added. The reaction vial was shaken for 4 h before THF removal via a stream of nitrogen. The aqueous residue was purified by preparative HPLC to yield compound (95) (62 mg). LCMS purity 95%, m/z 486 [M++H]+, 1H NMR (400 MHz, MeOD), δ:1.35 (4H, m, 2×CH2), 1.55-1.75 (4H, m, alkyl), 2.10 (2H, t, CH2), 2.35 (2H, t, CH2), 2.95 (2H, dd, CH), 3.20 (1H, dd, CH), 4.45 (1H, dd, NHCHCO), 5.00 (2H, s, CH2), 7.05 (1H, d, Ar), 7.20-7.35 (6H, m, Ar), 7.55 (2H, m, Ar).

Workup

  1. customThe reaction
  2. customThe aqueous residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-fe20fa2322854bfa9efa453d96cdbc69
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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