Sodium Hydroxide → HCID 57561712, compound

HRID 1434762Notes

Reaction equation

HRID 1434762 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH:15]2[CH:20]([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]2([CH3:23])[CH3:22])[NH:10][N:9]=1)=[O:7])C>CO>[CH3:23][C:16]1([CH3:22])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:21])[CH:15]1[CH2:14][CH2:13][C:11]1[NH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57561711HCID 57561711, compound

Product 1

HCID 57561712HCID 57561712, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 2.73 mmol) was added to a stirring, room temperature solution of 53 (0.1594 g, 0.5451 mmol) in MeOH (1.36 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (5 min). The reaction was concentrated, redissolved in H2O, and extracted with EtOAc. 10% aq. HCl was added dropwise to the aqueous layer until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 0.0119 g (8.2%) of 54. An additional 0.0590 g (40.9%) of 54 was obtained, although slightly impure, from the EtOAc layer. 1H (CD3OD, 400 MHz): δ 6.56 (1H, s), 2.64 (2H, t, J=7.8 Hz), 2.03-1.89 (1H, m), 1.69-1.53 (2H, m), 1.55-1.41 (2H, m), 1.39-1.27 (2H, m), 1.20-1.06 (3H, m), 0.97 (3H, s), 0.91 (3H, s), 0.86 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, 100 MHz): δ 165.07, 149.02, 143.33, 107.26, 50.24, 37.04, 35.11, 31.58, 31.33, 29.00, 28.87, 28.37, 26.30, 22.13, 18.90 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 29.00, 28.87, 18.90; CH2 carbons: 37.04, 31.33, 28.37, 26.30, 22.13; CH carbons: 107.26, 50.24, 31.58 ppm. HPLC: 10.497 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (5 min)
  4. concentrationThe reaction was concentrated
  5. dissolutionredissolved in H2O
  6. extractionextracted with EtOAc
  7. addition10% aq. HCl was added dropwise to the aqueous layer until the pH=2
  8. customThe white solid that precipitated from the reaction
  9. filtrationwas filtered off
  10. washwashed with cold H2O
  11. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-a732d98245f1454b9443720a739843f0
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

Loading…