Sodium Hydroxide → HCID 57561729, compound

HRID 1366934Notes

Reaction equation

HRID 1366934 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[NH:10][N:9]=1)=[O:7])C>CO>[C:16]1([C@@H:14]([CH3:15])[CH2:13][C:11]2[NH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57561745HCID 57561745, compound

Product 1

HCID 57561729HCID 57561729, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 11.9 mmol) was added to a stirring, room temperature solution of 79 (0.6153 g, 0.2.38 mmol) in MeOH (6 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (7 min): The reaction was concentrated, redissolved in H2O, and extracted with EtOAc (1 mL): 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 0.250 g (45.6%) of 80. 1H (CD3OD, 400 MHz): δ 7.30-7.23 (2H, m), 7.22-7.13 (3H, m), 6.62 (1H, s), 3.14 (1H, app sex, J=7.3 Hz), 3.03 (2H, d, J=7.8 Hz), 1.31 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, 100 MHz): δ 162.00, 149.20, 146.35, 141.76, 129.62, 127.93, 127.64, 109.16, 41.21, 35.22, 22.11 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 22.11; CH2 carbons: 35.22; CH carbons: 129.62, 127.93, 127.64, 109.16, 41.21 ppm. HPLC: 8.771 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (7 min)
  4. concentrationThe reaction was concentrated
  5. dissolutionredissolved in H2O
  6. extractionextracted with EtOAc (1 mL)
  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-a8513a6b3660401a8b55f05b189a297f
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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