Sodium Hydroxide → HCID 178451887, compound

HRID 1957585Notes

Reaction equation

HRID 1957585 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([S:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[NH:9][CH:10]=1)=[O:5])C.CO.[OH-].[Na+].[OH-].[Na+]>>[C:20]([N:17]1[CH2:16][CH2:15][CH:14]([CH2:13][CH2:12][S:11][C:8]2[NH:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH2:19][CH2:18]1)([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21]

Participants

4

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 23721981Sodium hydroxide methanolHCID 178469907HCID 178469907, compound

Product 1

HCID 178451887HCID 178451887, compound

Procedure

6-2 (162.5 mg, 0.42 mmol) was dissolved in 3 mL MeOH NaOH (1N, 0.5 mL, 0.5 mmol) was added; after 6 h additional NaOH (1N, 1 mL, 1 mmol) was added; after 1 day additional NaOH (1N, 1 mL, 1 mmol) was added. After three more days the mixture was heated at 50° for 6 h, then concentrated. The residue was taken up in water, pH adjusted to 5 with 5% KHSO4, extracted 3× with EtOAc, the combined organic extracts were washed with brine, dried (MgSO4), and concentrated providing acid 6-3. Rf 0.39 (9:1:1 CH2Cl2 /MeOH/HOAc);

Workup

  1. additionwas added
  2. temperatureAfter three more days the mixture was heated at 50° for 6 h
  3. concentrationconcentrated
  4. extractionextracted 3× with EtOAc
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4ee586a56290494598c89ad2356f70bc
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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