Acetic Acid → HCID 7299381, compound

HRID 2237373Notes

Reaction equation

HRID 2237373 reaction equation
C[O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH:25]([CH3:27])[CH3:26])[NH:5][C:6](=[O:23])[C@@H:7]([CH2:19][CH:20]([CH3:22])[CH3:21])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].O.[OH-].[Li+].C(O)(=O)C>C1COCC1.O>[CH2:12]([O:11][C:9]([NH:8][C@@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:28])=[O:2])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:23])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 7237625HCID 7237625, compound

Product 1

HCID 7299381HCID 7299381, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

N-(Benzyloxycarbonyl)-D-leucyl-L-leucine methyl ester (Example 29A, 1.12 g, 2.85 mmol) is provided at 0° C. in THF/water 2:1 (15 ml) and then lithium hydroxide monohydrate (140 mg, 5.71 mmol, 2 equivalents) is added. When the HPLC chromatogram (Method 2) shows complete conversion (about 1 h), the reaction mixture is adjusted to pH 3-4 with acetic acid, concentrated in vacuo under cold conditions and then freed of solvent by freeze-drying overnight. The crude product is purified by means of preparative HPLC (Method 13) whereby 958 mg (88.7% of theory) of the title compound are obtained.

Workup

  1. customconversion (about 1 h)
  2. concentrationconcentrated in vacuo under cold conditions
  3. customby freeze-drying overnight
  4. customThe crude product is purified by means of preparative HPLC (Method 13) whereby 958 mg (88.7% of theory) of the title compound
  5. customare obtained

Sources & evidence

ORD record
ord-15c99cdeca3947ddbfab9fe067cd5e7c
Source dataset
uspto-grants-2010_05
Patent number
US07718611B2

Reaction notes

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