Sodium Hydroxide → HCID 68579989, compound

HRID 644307Notes

Reaction equation

HRID 644307 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:36])[CH2:22][CH2:21]2)=[O:19])[C:13]([O:15]C)=[O:14])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2].[OH-].[Na+]>CO>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:36])[CH2:22][CH2:21]2)=[O:19])[C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68579999HCID 68579999, compound

Product 1

HCID 68579989HCID 68579989, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude product (6 g, 11.84 mmol) described in 7a) was placed in 120 mL MeOH, combined with 40 mL 1M NaOH (40 mmol) and refluxed for 5 h. The reaction mixture was concentrated by evaporation in vacuo, the residue was combined with 150 mL of water and 40 mL 1M HCl, exhaustively extracted with DCM and the combined organic phases were dried over MgSO4. After elimination of the desiccant and solvent the residue was triturated with diisopropylether and suction filtered.

Workup

  1. temperaturerefluxed for 5 h
  2. concentrationThe reaction mixture was concentrated by evaporation in vacuo
  3. extractionexhaustively extracted with DCM
  4. dry with materialthe combined organic phases were dried over MgSO4
  5. customAfter elimination of the desiccant and solvent the residue was triturated with diisopropylether and suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5a6e9f87cf8c4559a698c5abee222930
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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