Hydrochloric Acid → HCID 131720451, compound

HRID 2393048Notes

Reaction equation

HRID 2393048 reaction equation
[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH:18]([C:23](C(OCC)=O)=[O:24])[CH2:19][CH2:20][CH2:21][CH3:22])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH-:40].[Na+].Cl>CO>[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH:18]([C:23]([OH:24])=[O:40])[CH2:19][CH2:20][CH2:21][CH3:22])=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131720452HCID 131720452, compound

Product 1

HCID 131720451HCID 131720451, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-Cbz-L-Leu-L-Leu-DL-Nle-CO2Et (1.0 eq), as prepared in Example 5, in methanol at R.T. is added 1N NaOH (1.1 eq). The mixture is stirred for 6 h. The reaction mixture is cooled to 0° C., acidified with 1N HCl (pH=3) and extracted with EA. The organic extracts are washed with water, dried (MgSO4), filtered and concentrated to give a crude residue. Trituration with hexane and drying in vacuo gives the title compound, N-Cbz-L-Leu-L-Leu-DL-Nle-CO2H.

Workup

  1. extractionextracted with EA
  2. washThe organic extracts are washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude residue
  7. dry with materialTrituration with hexane and drying in vacuo

Sources & evidence

ORD record
ord-87ad947963e0493d9312009f11995c46
Source dataset
uspto-grants-1998_09
Patent number
US05804560

Reaction notes

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