Diazomethane → Methyl benzyloxycarbonyl-isoleucyl-prolyl-prolinate

HRID 1282959Notes

Reaction equation

HRID 1282959 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21](O)=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([OH:31])=[O:30].[N+](=[CH2:37])=[N-]>CO.C(O)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([O:31][CH3:37])=[O:30])=[O:22])=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 68146244Benzyloxycarbonyl-isoleucyl-proline proline

Product 1

HCID 68146169Methyl benzyloxycarbonyl-isoleucyl-prolyl-prolinate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

The tripeptide acid of Example 1 (4.6 g) is dissolved in methanol and treated with an ethereal solution of diazomethane until a persistent yellow color is obtained. After 0.5 hour a few drops of acetic acid are added to discharge the yellow color; the solvent is removed in vacuo and replaced with ethyl acetate. This solution is washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate and water. The organic phase is dried over magnesium sulfate and concentrated to dryness to yield the title compound.

Workup

  1. customis obtained
  2. customthe solvent is removed in vacuo
  3. washThis solution is washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate and water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-327b6da7936c4b3485c62d4ef6052151
Source dataset
uspto-grants-1976_08
Patent number
US03973006

Reaction notes

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