Sodium Hydroxide → HCID 66717364, compound

HRID 2359798Notes

Reaction equation

HRID 2359798 reaction equation
C([O:5][C:6](=[O:46])[CH2:7][N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[S:34][C:35]([CH3:38])=[CH:36][N:37]=3)=[CH:29][CH:28]=2)[NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:19])=[O:18])[N:10]=1)(C)(C)C.[OH-].[Na+]>O>[CH3:38][C:35]1[S:34][C:33]([C:30]2[CH:29]=[CH:28][C:27]([CH2:26][CH:15]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)(=[O:18])=[O:19])[C:11]3[N:10]=[C:9]([NH:8][CH2:7][C:6]([OH:46])=[O:5])[CH:14]=[CH:13][CH:12]=3)=[CH:32][CH:31]=2)=[N:37][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86651783HCID 86651783, compound

Product 1

HCID 66717364HCID 66717364, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reaction was carried out in the same manner as in Example 19-(b) except for using tert-butyl[tert-butoxycarbonyl(6-{[4-(5-methylthiazol-2-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetate (269 mg, 0.404 mmol) obtained in Example 22-(c) in place of tert-butyl[tert-butoxycarbonyl(6-{[4-(pyridin-2-yl)benzyl]-(pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetate. After completion of the reaction, water (20 ml) was added to the reaction solution, then it was adjusted to pH 10.9 with a 1N aqueous sodium hydroxide solution, and subsequently insolubles were filtered off. The filtrate was adjusted to pH 5.6 with 1N hydrochloric acid, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the resulting residue were added tert-butyl methyl ether (1 ml) and diisopropyl ether (10 ml), followed by sonication. A precipitated solid was collected by aeration, and then dried under reduced pressure to afford the title compound (113 mg) as a white solid. (Yield: 55%)

Workup

  1. customReaction
  2. additionwas added to the reaction solution
  3. filtrationwere filtered off
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the resulting residue were added tert-butyl methyl ether (1 ml) and diisopropyl ether (10 ml)
  8. customfollowed by sonication
  9. customA precipitated solid was collected by aeration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-a586ee0bb6534a568aebc9df88cf6a5d
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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