HCID 54349521, compound → HCID 57178210, compound

HRID 965157Notes

Reaction equation

HRID 965157 reaction equation
C([O:8][NH:9][C:10](=[O:40])[CH2:11][C@H:12]([C:17](=[O:39])[NH:18][C@H:19]1[CH2:36][CH:35]2[CH2:37][N:28]([CH:29]3[CH:34]2[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:38])[CH2:13][CH:14]([CH3:16])[CH3:15])C1C=CC=CC=1>C(O)C.CO.CCOCC.[Pd]>[OH:8][NH:9][C:10](=[O:40])[CH2:11][C@H:12]([C:17](=[O:39])[NH:18][C@H:19]1[CH2:36][CH:35]2[CH2:37][N:28]([CH:29]3[CH:34]2[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:38])[CH2:13][CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 1

HCID 54349521HCID 54349521, compound

Product 1

HCID 57178210HCID 57178210, compoundYield 91%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(3R,10S)-N-benzyloxy-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadecan-10-ylcarbamoyl)hexanamide (75 mg, 0.135 mmol) was hydrogenated at 1 atm H2 pressure in absolute ethanol (5 mL) in the presence of 10% Pd-C (35 mg) for 2 hours. Argon gas was bubbled into the reaction mixture for 10 minutes and the reaction mixture was filtered through a cone of celite. The catalyst on celite was further washed with 5 mL of ethanol. The combined filtrate was evaporated to dryness to afford a solid residue. The solid was stirred in 10 mL of 5% MeOH in ether at 0° C. for 30 mins and filtered to yield 57 mg (91%) of (3R,10S)-N-hydroxy-5-methyl-3-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadecan-10-ylcarbamoyl) hexanamide, as an off-white powder, MS: 465 (M+H)+.

Workup

  1. customArgon gas was bubbled into the reaction mixture for 10 minutes
  2. filtrationthe reaction mixture was filtered through a cone of celite
  3. washThe catalyst on celite was further washed with 5 mL of ethanol
  4. customThe combined filtrate was evaporated to dryness
  5. customto afford a solid residue
  6. filtrationfiltered

Sources & evidence

ORD record
ord-13ac3ba624fe40c28c2bc965778ecf4a
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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