Sodium Hydroxide → HCID 22872862, compound

HRID 1780816Notes

Reaction equation

HRID 1780816 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][S:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:10][NH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17]C)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][S:23][C:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:10][NH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22872871HCID 22872871, compound

Product 1

HCID 22872862HCID 22872862, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 24 (1.51 g) in methanol (70 mL) was added 5% sodium hydroxide (10 mL). The solution was stirred for 18 h, concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to obtain the product. NMR (300 MHz, CDCl3) δ 7.50-7.10 (18H, m), 6.76 (1H, m,), 4.60 (1H, m), 3.82 (1H, m), 3.08 (2H, m), 2.47 (3H, m), 1.43 (9H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain the product

Sources & evidence

ORD record
ord-818da81c89a54507856f80bb12ec3774
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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