HCID 18651488, compound → HCID 178453551, compound

HRID 1591426Notes

Reaction equation

HRID 1591426 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([NH:13][C@@H:14]1[CH2:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]3[N:42](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:41]=[N:40][N:39]=3)=[CH:28][CH:27]=2)[C:15]1=[O:62])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([NH:13][CH:14]1[CH2:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]3[NH:42][N:41]=[N:40][N:39]=3)=[CH:30][CH:31]=2)[C:15]1=[O:62])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18651488HCID 18651488, compound

Product 1

HCID 178453551HCID 178453551, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The intermediate obtained in Step B (150 mg, 0.18 mmol) dissolved in 5 mL methanol was hydrogenated over 30 mg of Pd(OH)2 on carbon at one atmosphere for 2 hours. The mixture was filtered through Celite and the filtrate concentrated under vacuum. The residue was purified by medium pressure liquid chromatography on silica, eluting with ethyl acetate/acetonitrile/methanol (9:1:1) to afford 62 mg (0.11 mmol, 59%) of the product as a colorless glass. 1H NMR (200 MHz, CD3OD): 1.39 (s,9H), 2.0-2.5 (m,6H), 3.26 (t,7 Hz,2H), 4.31 (dd;7,12 Hz;1H), 4.83 (d,16 Hz,1H), 5.20 (d,16 Hz,1H), 6.98 (d,8 Hz,2H), 7.1-7.6 (m,10H). FAB-MS: calc. for C32H35N7O4 581; found 582 (M+H,19%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe residue was purified by medium pressure liquid chromatography on silica
  4. washeluting with ethyl acetate/acetonitrile/methanol (9:1:1)

Sources & evidence

ORD record
ord-4d3815ed9c224615a37201231cb9efd7
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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