HCID 86595550, compound → HCID 44446839, compound

HRID 1664620Notes

Reaction equation

HRID 1664620 reaction equation
C([O:8][NH:9][C:10]([C@H:12]1[CH2:19][C:16]2([CH2:18][CH2:17]2)[CH2:15][N:14]([C:20]([O:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:21])[C@@H:13]1[C:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:33][CH2:32]1)=[O:30])=[O:11])C1C=CC=CC=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[OH:8][NH:9][C:10]([C@H:12]1[CH2:19][C:16]2([CH2:17][CH2:18]2)[CH2:15][N:14]([C:20]([O:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:21])[C@@H:13]1[C:29]([N:31]1[CH2:32][CH2:33][N:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:35][CH2:36]1)=[O:30])=[O:11]

Participants

4

Reactant 1

HCID 86595550HCID 86595550, compound

Product 1

HCID 44446839HCID 44446839, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

Tetrahydro-2H-pyran-4-yl(6S,7S)-7-(((benzyloxy)amino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate (6.0 mg, 0.0104 mmole) was dissolved in methanol (0.3 ml) and 2 mg of 5% Pd/BaSO4 was added to the resulting reaction mixture. The mixture was stirred under hydrogen (1 atm) for 1.5 hours. After filtration, the product was purified with prep. RP-HPLC. The desired fractions were collected and freeze dried to give 3.8 mg solid. LC-MS: m/z 487.1 (M+H)+; 509.0 (M+Na)+.

Workup

  1. filtrationAfter filtration
  2. customthe product was purified with prep
  3. customThe desired fractions were collected
  4. customfreeze dried

Sources & evidence

ORD record
ord-bd018a679e9a442abb290b24a4876df0
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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