Lithium Hydroxide → HCID 59708800, compound

HRID 1097295Notes

Reaction equation

HRID 1097295 reaction equation
[OH-:1].[Li+].C[O:4][C:5](=[O:30])[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])[CH2:11][CH2:10]1>O1CCCC1>[C:5]([CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([OH:29])=[O:1])[CH2:11][CH2:10]1)([OH:4])=[O:30]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59708791HCID 59708791, compound

Product 1

HCID 59708800HCID 59708800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide (5 mL of a 4 M solution) was added to a solution of 11 (2.50 g, 6.50 mmol) stirring in tetrahydrofuran (40 mL). The reaction mixture was stirred at ambient temperature for 4 hours. The solvent was removed under vacuum and the residue dissolved in water (25 mL) and extracted with dichloromethane (1×25 mL). The aqueous solution was acidified to pH 6 as indicated by pH paper and extracted with ethyl acetate (3×25 mL). The acidic aqueous solution was evaporated to dryness and dried under vacuum to give the carboxylic acid 12 (3.58 g, quantitative yield) as a yellow foam: 1H NMR (300 MHz, CD3OD) δ 1.61-1.89 (m, 6H), 2.27-2.38 (m, 2H), 2.75-3.09 (m, 10H), 3.33-3.35 (m, 6H), 3.41 (t, J=6.3 Hz, 2H), 7.38-7.47 (m, 3H), 7.62-7.65 (m, 1H); ESI MS m/z 392 [C20H29N3O5+H]+.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue dissolved in water (25 mL)
  3. extractionextracted with dichloromethane (1×25 mL)
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. customThe acidic aqueous solution was evaporated to dryness
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6754a7d8f72a416b819b2170a456ceef
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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