Sodium Hydroxide → HCID 18654886, compound

HRID 2226385Notes

Reaction equation

HRID 2226385 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH:24]2[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:18][C@H:17]1[C:25]([O:27]CC)=[O:26])=[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[CH:24]2[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:18][C@H:17]1[C:25]([OH:27])=[O:26])=[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 67788724HCID 67788724, compound

Product 1

HCID 18654886HCID 18654886, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.22 g of 1-[N-benzyloxycarbonyl-(S)-alanyl]octahydroindole-2(S)-carboxylic acid, ethyl ester in 150 ml of methanol, add 20 ml of 2.5N sodium hydroxide and stir the mixture at room temperature for 18 hours. Concentrate the mixture under nitrogen, dilute the residue with ice-water and then make the mixture acidic with concentrated hydrochloric acid. Extract the aqueous solution with ethyl acetate and dry the organic phase over magnesium sulfate. Concentrate the organic phase and place it on a column of silica gel (500 g., 60-200 mesh). Elute with chloroform:glacial acetic acid 9:1 to give 1- [N-benzyloxycarbonyl-(S)-alanyl ]octahydroindole-2(S)-carboxylic acid, a white solid [α]D26 62.1° (ethanol), m.p. 58.60°.

Workup

  1. concentrationConcentrate the mixture under nitrogen
  2. additiondilute the residue with ice-water
  3. extractionExtract the aqueous solution with ethyl acetate
  4. dry with materialdry the organic phase over magnesium sulfate
  5. concentrationConcentrate the organic phase and place it on a column of silica gel (500 g., 60-200 mesh)
  6. washElute with chloroform

Sources & evidence

ORD record
ord-32a74e4db49f4990a1317c061a348cf2
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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