Sodium Hydroxide → HCID 10906061, compound

HRID 1981931Notes

Reaction equation

HRID 1981931 reaction equation
[NH:1]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][CH2:18][C:19]([O:21]CC)=[O:20])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3].[OH-].[Na+]>O1CCOCC1>[C:24]([NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:3])([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70445821HCID 70445821, compound

Product 1

HCID 10906061HCID 10906061, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 350 ml of dioxane, 30 g of Z-Ala-Phe-Gly-OEt was added, followed by addition of 70 ml of lN-NaOH. The reaction solution was dissolved at room temperature. After one hour's reaction, almost all the dioxane was removed by distillation, followed by neutralization with 70 ml of lN-HCl. The resulting mixture was well extracted with ethyl acetate. The extract was dried over MgSO4 and the solvent was removed by distillation to give carbobenzoxy-alanyl-phenylalanyl-glycine having a melting point of 168°-171° C. and [α]D25 =-20.1° (C=1.0, DMF) in yield of 27.0 g (96%).

Workup

  1. dissolutionThe reaction solution was dissolved at room temperature
  2. customAfter one hour's reaction
  3. customalmost all the dioxane was removed by distillation
  4. extractionThe resulting mixture was well extracted with ethyl acetate
  5. dry with materialThe extract was dried over MgSO4
  6. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-dc7c13137dde4241ae7601e6841cb7c1
Source dataset
uspto-grants-1986_06
Patent number
US04594409

Reaction notes

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