Sodium Hydroxide → HCID 15614980, compound

HRID 620226Notes

Reaction equation

HRID 620226 reaction equation
[C:1]([NH:11][C@H:12]([C:14]([N:16]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2)[CH2:17][C:18]([O:20]CC)=[O:19])=[O:15])[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[OH-].[Na+]>C(O)C>[C:1]([NH:11][C@H:12]([C:14]([N:16]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2)[CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH3:13])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15614978HCID 15614978, compound

Product 1

HCID 15614980HCID 15614980, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl N-carbobenzoxy-L-alanyl-N-(5-indanyl)-glycinate (14.0 g, 33.0 mmol) in 150 ml ethanol was added sodium hydroxide (25 ml of a 2N aqueous solution, 49.5 mmol) and mixture stirred at room temperature for 20 h. The volatiles were removed under reduced pressure and the residue dissolved in ether and saturated sodium bicarbonate. The organic layer was separated and extracted with saturated sodium bicarbonate. The combined basic extracts were cooled in an ice bath and acidified with concentrated HCl. The aqueous solution was extracted thoroughly with CH2Cl2. The combined organic extracts were dried (MgSO4) and concentrated in vacuo.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue dissolved in ether
  3. customThe organic layer was separated
  4. extractionextracted with saturated sodium bicarbonate
  5. temperatureThe combined basic extracts were cooled in an ice bath
  6. extractionThe aqueous solution was extracted thoroughly with CH2Cl2
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da701ad6601d4ca19cfee56ecda277b5
Source dataset
uspto-grants-1989_04
Patent number
US04820729

Reaction notes

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