Nitrogen → HCID 15940510, compound

HRID 548254Notes

Reaction equation

HRID 548254 reaction equation
C1([O:6][C:7](=[O:35])[C@@H:8]([NH:13][C:14](=[O:34])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:33])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](=[O:32])[NH:30][OH:31])=[CH:17][CH:16]=2)[CH2:9][CH:10]([CH3:12])[CH3:11])CCCC1.[OH-].[Na+].N#N>C1COCC1>[OH:31][NH:30][C:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([NH:13][C@@H:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[C:7]([OH:35])=[O:6])=[O:34])=[CH:20][CH:19]=1)=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 15940509HCID 15940509, compound

Product 1

HCID 15940510HCID 15940510, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound (98) (21 mg, 0.043 mmol) was dissolved in THF (1 ml) and 2M NaOH (1 ml) added. The reaction vial was shaken for 16 h before THF removal by blowing a stream of N2 gas at the surface of the solution. The aqueous residue was purified by preparative HPLC to yield compound (99) (5.2 mg). LCMS purity 92%, m/z 422 [M++H]+, 1H NMR (400 MHz, MeOD), δ: 0.95-1.05 (6H, m, 2×CH3), 1.30-1.50 (4 H, m, alkyl), 1.55-1.85 (7H, m, alkyl), 2.10 (2H, t, CH2), 2.40 (2H, t, CH2), 4.65 (1 H, m, CH), 7.65 (2H, d, Ar), 7.80 (2H, d, Ar).

Workup

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

Sources & evidence

ORD record
ord-3cf60b2336b14b0b9293831f54209904
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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