Hydrochloric Acid → HCID 58664828, compound

HRID 254367Notes

Reaction equation

HRID 254367 reaction equation
C[O:2][C:3](=[O:27])[C@H:4]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:5]#[C:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])=[CH:10][CH:9]=1.O.[OH-].[Li+].Cl>CO.C1COCC1.O>[NH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH2:5][C@@H:4]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:3]([OH:27])=[O:2])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66849709HCID 66849709, compound

Product 1

HCID 58664828HCID 58664828, compoundYield 102%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 240 (0.40 g, 0.780 mmol) was dissolved in a mixture of methanol and THF (10 mL, 1/1, v/v). To the solution was added lithium hydroxide monohydrate (0.063 g, 1.561 mmol) dissolved in water (1 mL). The reaction mixture was stirred at room temperature for two hours, and then neutralized with 2N aqueous HCl solution to pH 5. The mixture was then concentrated under vacuum. The residue was taken into ethanol (3 mL) and the resulting solution was concentrated again under vacuum. The procedure was repeated two more times to ensure no aqueous solvent remained. The residue was chromatographed over silica gel, eluting with a mixture of concentrated ammonium hydroxide (0-10%), methanol (0-30%), and dichloromethane (100-60%), to afford the product 280 (0.29 g, 75%) as a white solid. 1H NMR (300 MHz, CD3OD): δ 1.46 (s, 9H), 1.58-1.78 (m, 8H), 2.54-2.68 (m, 4H), 2.85 (t, J=6.6 Hz, 2H), 3.98 (t, J=6.5 Hz, 1H), 7.08 (s, 4H), 8.50 (s, 1H). m/z (APCI) 365 [C20H32N2O4+H]+.

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. concentrationthe resulting solution was concentrated again under vacuum
  3. customThe residue was chromatographed over silica gel
  4. washeluting with a mixture of concentrated ammonium hydroxide (0-10%), methanol (0-30%), and dichloromethane (100-60%)

Sources & evidence

ORD record
ord-c193e61d82df408f9b0f2ca648653386
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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