Sodium Hydroxide → HCID 13373614, compound

HRID 2226403Notes

Reaction equation

HRID 2226403 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[C@H:24]([C:25]([O:27]C)=[O:26])[CH2:23][C:18]2([S:22][CH2:21][CH2:20][S:19]2)[CH2:17]1)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[C@H:24]([C:25]([OH:27])=[O:26])[CH2:23][C:18]2([S:19][CH2:20][CH2:21][S:22]2)[CH2:17]1)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13373612HCID 13373612, compound

Product 1

HCID 13373614HCID 13373614, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1.05 g of 7-[N-benzyloxycarbonyl-(S)-alanyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid, methyl ester in 100 ml of methanol. Add 10 ml of 2.5N sodium hydroxide and stir the mixture at room temperature for sixteen hours. Concentrate the mixture under nitrogen, dissolve the oil in 0.1N sodium hydroxide and dilute with ice water. Extract the aqueous solution with ethyl acetate. Acidify the aqueous solution with concentrated hydrochloric acid and then extract with ethyl acetate. Dry the organic phase over magnesium sulfate and concentrate it. Place the residue on a column of silica gel (100 g, 60-200 mesh) and elute with chloroform:glacial acetic acid 19:1 to obtain 7-[N-benzyloxycarbonyl-(S) -alanyl]-1,4-dithia-7-azaspiro-[4.4]nonane-8(S)-carboxylic acid, [α]D26 -15.8° (ethanol).

Workup

  1. concentrationConcentrate the mixture under nitrogen
  2. dissolutiondissolve the oil in 0.1N sodium hydroxide
  3. additiondilute with ice water
  4. extractionExtract the aqueous solution with ethyl acetate
  5. extractionextract with ethyl acetate
  6. dry with materialDry the organic phase over magnesium sulfate
  7. concentrationconcentrate it
  8. washelute with chloroform

Sources & evidence

ORD record
ord-821c16b8608241cab87308b0c0c5c3fa
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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