Methanol → HCID 58908003, compound

HRID 1295532Notes

Reaction equation

HRID 1295532 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:17][C@@:16]([C:28](=[O:31])[NH:29][CH3:30])([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[O:15][C:13]1=[O:14])=O)C1C=CC=CC=1.[H][H].C[OH:35]>[Pd]>[NH2:11][C@H:12]([CH2:17][C@@:16]([OH:15])([C:28](=[O:31])[NH:29][CH3:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[C:13]([OH:14])=[O:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 69119526HCID 69119526, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58908003HCID 58908003, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The aforementioned (2R,4R)-2-benzyloxycarbonylamino-4-methylcarbamoyl-4-(3-indolylmethyl)-γ-butyrolactone in an amount of 897 mg was dissolved in 40 ml of methanol, and 400 mg of 10% Pd—C was added thereto. Reduction was performed at room temperature in an atmosphere of hydrogen at ordinary pressure for 1 hour. After removing the catalyst by filtration, the reaction solution was vacuum concentrated. The residue was dissolved in 15 ml of ethanol, and 1.9 ml of a 2 N sodium hydroxide solution was added followed by stirring for a while. The reaction solution was vacuum concentrated and the residue was dissolved in 5 ml of water. The pH of the resulting solution was adjusted with a 2 N hydrochloric acid solution to be slightly acidic. Ethanol was then added and the deposited crystals were filtered resulting in 360 mg of (2R,4R)-2-amino-4-hydroxy-4-methylcarbamoyl-4-(3-indolylmethyl)butyric acid (1.18 mmol) as a crystal (Compound No. 7 in Table 1).

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 15 ml of ethanol
  5. addition1.9 ml of a 2 N sodium hydroxide solution was added
  6. concentrationconcentrated
  7. dissolutionthe residue was dissolved in 5 ml of water
  8. additionEthanol was then added
  9. filtrationthe deposited crystals were filtered

Sources & evidence

ORD record
ord-38b17f834ed1417b93d198a977e152aa
Source dataset
uspto-grants-2007_07
Patent number
US07244462B2

Reaction notes

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