HCID 70626619, compound → HCID 131711382, compound

HRID 66212Notes

Reaction equation

HRID 66212 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[C:15]2[N:14]([C:16](=[O:18])[CH3:17])[C:13](=[O:19])[N:12]([C:20](=[O:22])[CH3:21])[C:11]=2[CH2:10][S:9]1>C(OC(=O)C)(=O)C.[Pt]=O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:15]2[CH:11]([N:12]([C:20](=[O:22])[CH3:21])[C:13](=[O:19])[N:14]2[C:16](=[O:18])[CH3:17])[CH2:10][S:9]1

Participants

4

Reactant 1

HCID 70626619HCID 70626619, compound

Product 1

HCID 131711382HCID 131711382, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 7918Acetic AnhydrideSolvent2×

Procedure

In a 50 ml glass liner charged 12.8 mg of platinum oxide dampened with acetic anhydride. 417.7 mgs of N,N'-diacetyldehydrobiotin methyl ester high in the 1-isomer were added. The mixture was diluted to 50 ml with acetic anhydride. Hydrogenation was carried out at 550 psi of H2, 85° C., for 6 hours. After cooling the mixture was filtered through Celite removing the Pt metal. Stripping of solvent yielded a colorless oil. Analysis showed ~20% of starting material and 80% of reduction product high in the 1-isomer proportional to that in the starting material.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered through Celite
  3. customremoving the Pt metal
  4. customyielded a colorless oil

Sources & evidence

ORD record
ord-1cf0d9a4064f44cdb505611f697c0355
Source dataset
uspto-grants-1978_12
Patent number
US04130712

Reaction notes

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