HCID 66882720, compound → HCID 66881155, compound

HRID 1784031Notes

Reaction equation

HRID 1784031 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C:8](=[CH2:10])[CH2:7][C@H:6]1[C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:4]>CO.[OH-].[Na+]>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:11]([C@@H:6]2[CH2:7][C:8](=[CH2:10])[CH2:9][C@H:5]2[C:3]([OH:4])=[O:2])=[O:20])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 66882720HCID 66882720, compound

Product 1

HCID 66881155HCID 66881155, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The crude material 1b (13.7 g) was dissolved in 200 ml of MeOH and 20 ml of 7 N NaOH, the solution was stirred at 22° C. for 2 h and evaporated. The residue was partitioned between 0.1 N NaOH and CH2Cl2, the aqueous layer was washed with CH2Cl2 and the aqueous layer was acidified with 25% HCl, the suspension was filtered and the residue dried to give 11.0 g (45% overall) of the pure title compound 1c as a pale brown solid. MS: 278.3 (M−H)−.

Workup

  1. customevaporated
  2. customThe residue was partitioned between 0.1 N NaOH and CH2Cl2
  3. washthe aqueous layer was washed with CH2Cl2
  4. filtrationthe suspension was filtered
  5. customthe residue dried

Sources & evidence

ORD record
ord-a779344bc4d8422e9828f1a68c0addd9
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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