Sodium Hydroxide → HCID 15231787, compound

HRID 274947Notes

Reaction equation

HRID 274947 reaction equation
[C:1]([CH:6]([C:33]1[CH:38]=[C:37]([O:39][CH3:40])[C:36]2[O:41][CH2:42][O:43][C:35]=2[CH:34]=1)[O:7][C:8]1[C:13]([CH2:14][CH2:15][CH3:16])=[CH:12][C:11]([CH2:17][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]([CH2:27][CH3:28])[C:19]2=[O:29])=[CH:10][C:9]=1[CH2:30][CH2:31][CH3:32])([O:3]CC)=[O:2].[OH-].[Na+]>CO>[C:1]([CH:6]([C:33]1[CH:38]=[C:37]([O:39][CH3:40])[C:36]2[O:41][CH2:42][O:43][C:35]=2[CH:34]=1)[O:7][C:8]1[C:9]([CH2:30][CH2:31][CH3:32])=[CH:10][C:11]([CH2:17][N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]([CH2:27][CH3:28])[C:19]2=[O:29])=[CH:12][C:13]=1[CH2:14][CH2:15][CH3:16])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15231795HCID 15231795, compound

Product 1

HCID 15231787HCID 15231787, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step D was taken up in 10 mL of methanol and 4 mL 5N NaOH(aq) was added with stirring at room temperature. The reaction was stirred for 3 hours and the volatiles removed in vacuo. The resultant slurry was diluted with 50 mL H2O and acidified with 1N HCl (aq) and extracted with 3×20 mL ethyl acetate. The combined organics were concentrated in vacuo. Trituration of the resultant oil with ethyl ether gave 64 mg (82%-2 steps) of the title compound as a white solid.

Workup

  1. stirringThe reaction was stirred for 3 hours
  2. customthe volatiles removed in vacuo
  3. additionThe resultant slurry was diluted with 50 mL H2O
  4. extractionextracted with 3×20 mL ethyl acetate
  5. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-881f9397d7ef4710a3aff7434df7d9c1
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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