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 849738Notes

Reaction equation

HRID 849738 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 (Pt2O) 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)-.

Workup

  1. customArgon gas was bubbled into the reaction mixture for 15 mins
  2. filtrationand the catalyst (Pt2O) 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-195b4b5126484ac29081cbb0f5b127a8
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

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