Methanol → HCID 178449518, compound

HRID 841140Notes

Reaction equation

HRID 841140 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:36][C:37]1[N:38]=[CH:39][NH:40][CH:41]=1)[C:13]([N:15]([CH2:22][C:23]([NH:25][CH2:26][C:27]([CH3:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:28])=[O:24])[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.O.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:36][C:37]1[N:38]=[CH:39][NH:40][CH:41]=1)[C:13]([N:15]([CH2:22][C:23]([NH:25][CH2:26][C:27]([CH3:28])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:35])=[O:24])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 178500811methyl 3-([(2S)-2-[(benzyloxy)carbonyl]amino-3-(1H-4-imidazolyl)propanoyl]-2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethylamino)propanoate

Product 1

HCID 178449518HCID 178449518, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 4 (0.30 g, 0.53 mmol) was dissolved in tetrahydrofuran (10 mL), methanol (10 mL) and water (1 mL). Sodium hydroxide (42 mg, 1.05 mmol) was added and the reaction was stirred overnight at room temperature. The solution was concentrated in vacuo and the residue taken up in 0.1 M NaPO4 buffer (100 mL). The pH was brought to 6 by the addition of 1N HCl. The product was extracted three times with ethyl acetate. The ethyl acetate was washed twice with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification was carried out via reversed-phase HPLC (0.1 % trifluoroacetic acid in acetonitrile and 0.1% aqueous trifluoroacetic acid as eluent; C-18 column) to give a white powder; 0.078 g (27% yield). MS-APCI: M+1=550.3.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionThe pH was brought to 6 by the addition of 1N HCl
  3. extractionThe product was extracted three times with ethyl acetate
  4. washThe ethyl acetate was washed twice with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification
  9. customto give a white powder

Sources & evidence

ORD record
ord-35fe5d5dcb82491c945cda8a1ce8e0f2
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

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