5-Methyl-3-(9-oxo-1,8-diaza-tricyclo(10.6.1.013,18)nonadeca-12(19),13,15,17-tetraen-10-ylcarbamoyl)-hexanoic acid → (3R,10S)-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18]nonadecan-10-ylcarbamoyl)hexanoic acid

HRID 965156Notes

Reaction equation

HRID 965156 reaction equation
[CH3:1][CH:2]([CH3:32])[CH2:3][C@@H:4]([C:9](=[O:31])[NH:10][C@H:11]1[CH2:28][C:27]2=[CH:29][N:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=32)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:30])[CH2:5][C:6]([OH:8])=[O:7]>C(O)(=O)C>[CH3:1][CH:2]([CH3:32])[CH2:3][C@@H:4]([C:9](=[O:31])[NH:10][C@H:11]1[CH2:28][CH:27]2[CH2:29][N:20]([CH:21]3[CH:26]2[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:30])[CH2:5][C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 52893145-Methyl-3-(9-oxo-1,8-diaza-tricyclo(10.6.1.013,18)nonadeca-12(19),13,15,17-tetraen-10-ylcarbamoyl)-hexanoic acid

Product 1

HCID 57036580(3R,10S)-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18]nonadecan-10-ylcarbamoyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(3R,10S)-5-Methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid (200 mg, 0.45 mmol) was dissolved in 10 mL of glacial acetic acid and was hydrogenated at 100 psi H2 pressure in the presence of Pt2O (60 mg) in a Parr reactor at room temperature for 15 hrs. Argon gas was bubbled into the reaction mixture for 15 mins. and the catalyst (Pt2 O) was filtered off (through a cone of celite). The clear filtrate was evaporated to dryness and further co-evaporated with toluene twice to give quantitative yield of (3R,10S)-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadecan-10-ylcarbamoyl)hexanoic acid as a white solid. MS: 448 (M-H)31 .

Workup

  1. customArgon gas was bubbled into the reaction mixture for 15 mins
  2. filtrationand the catalyst (Pt2 O) was filtered off (through a cone of celite)
  3. customThe clear filtrate was evaporated to dryness and further co-evaporated with toluene twice

Sources & evidence

ORD record
ord-52c15582e0434e80829cf65cee730fca
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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