Sodium Hydroxide → HCID 20638913, compound

HRID 565407Notes

Reaction equation

HRID 565407 reaction equation
[CH3:1][N:2]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]C)=[O:24])[C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1.[OH-].[Na+]>CO>[CH3:1][N:2]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20638914HCID 20638914, compound

Product 1

HCID 20638913HCID 20638913, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 1 liter round bottom flask, charged with 11.58 g (30.0 mmol) of 13 in 100 mL of methanol was added 50 mL of 1N aqueous sodium hydroxide. The mixture was stirred for 2-3 h and then concentrated via rotary evaporation. The residue was transferred to a 250 mL round bottom flask in a total of 75 mL of de-ionized water. With vigorous stirring, the pH of the solution was adjusted to 1.5-2 by addition of 1N aqueous HCl, the product precipitating out as a white solid in the process. The mixture was vacuum filtered. The collected solids were rinsed with 3×50 mL aliquots of ice cold de-ionized water. The solids were air dried for 3 h and then under full vacuum pump pressure (<0.5 mm Hg) for 21 h to afford 10.07 g of the product (14) as a white solid (90%): 1H NMR (d6-DMSO) d 6.43 (1H, s), 6.35 (1H, s), 4.30 (1H, m), 4.12 (1H, m), 3.23 (2H, t), 3.10 (1H, m), 2.91 and 2.78 (3H, 2 s), 2.81 (1H, dd), 2.57 (1H, d), 2.30-2.13 (4H, m) and 1.79-1.10 (12H, m) ppm; 1H NMR (CD3OD) d 4.48 (1H, dd), 4.29 (1H, dd), 3.35 (2H, t), 3.19 (1H, m), 3.02 and 2.88 (3H, 2 s), 2.91 (1H, dd), 2.68 (1H, d), 2.43-2.23 (4H, m) and 1.83-1.21 (12H, m) ppm; Thin Layer Chromatography (Visualization with p-aminocinnimaldehyde spray); RP-18 Silica Gel, Rf=0.50 ({fraction (60/40)} methanol/water).

Workup

  1. concentrationconcentrated via rotary evaporation
  2. customThe residue was transferred to a 250 mL round bottom flask in a total of 75 mL of de-ionized water
  3. additionWith vigorous stirring, the pH of the solution was adjusted to 1.5-2 by addition of 1N aqueous HCl
  4. customthe product precipitating out as a white solid in the process
  5. filtrationfiltered
  6. washThe collected solids were rinsed with 3×50 mL aliquots of ice cold de-ionized water
  7. customdried for 3 h

Sources & evidence

ORD record
ord-ffbc0d32ee3e436995b5c1492e620ed7
Source dataset
uspto-grants-2001_01
Patent number
US06172045B2

Reaction notes

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