Sodium Hydroxide → HCID 13373614, compound

HRID 2417771Notes

Reaction equation

HRID 2417771 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 2.5 N sodium hydroxide and stir the mixture at room temperature for sixteen hours. Concentrate the mixture under nitrogen, dissolve the oil in 0.1 N sodium hydroxide and dilute with ice water. Adjust to pH2 with concentrated hydrochloric acid, 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 0.1 N sodium hydroxide
  3. additiondilute with ice water
  4. extractionextract with ethyl acetate
  5. dry with materialDry the organic phase over magnesium sulfate
  6. concentrationconcentrate it
  7. washelute with chloroform

Sources & evidence

ORD record
ord-532f2bb17eca4e77bc7ac84ed1a21484
Source dataset
uspto-grants-1984_09
Patent number
US04470972

Reaction notes

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