HCID 57385085, compound → HCID 67978738, compound

HRID 1895795Notes

Reaction equation

HRID 1895795 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=1)[CH2:5][C@@H:6]1[NH:31][C:30](=[O:32])[C@H:29]([CH:33]([CH3:35])[CH3:34])[NH:28][C:27](=[O:36])[C@H:26]([CH3:37])[C@H:25]([O:38][CH3:39])[CH2:24][CH2:23][CH:22]=[CH:21][C:20]2[CH:40]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C@@H:15]([CH3:41])[O:14][C:13](=[O:42])[C@H:12]2[NH:43][N:8]([CH2:9][CH2:10][CH2:11]2)[C:7]1=[O:44]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=1)[CH2:5][C@@H:6]1[NH:31][C:30](=[O:32])[C@H:29]([CH:33]([CH3:35])[CH3:34])[NH:28][C:27](=[O:36])[C@H:26]([CH3:37])[C@H:25]([O:38][CH3:39])[CH2:24][CH2:23][CH2:22][CH2:21][C:20]2[CH:40]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C@@H:15]([CH3:41])[O:14][C:13](=[O:42])[C@H:12]2[NH:43][N:8]([CH2:9][CH2:10][CH2:11]2)[C:7]1=[O:44]

Participants

4

Reactant 1

HCID 57385085HCID 57385085, compound

Product 1

HCID 67978738HCID 67978738, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-(2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(27),21,23,25-tetraene-4,10,13,16-tetraone (12 mg, 0.0185 mmol) in ethyl acetate (2 mL) containing 10% palladium on carbon (10 mg) was hydrogenated at room temperature and pressure for 1 hour. The reaction mixture was filtered through filter aid and the filter pad was washed with ethyl acetate. The filtrate was evaporated and the residue was purified by silica gel chromatography using iso-hexanes/ethyl acetate 4:6 to afford the title compound (5.6 mg, 47%) as a white solid. 1H NMR (300 MHz, CD3CN) δ0.95 (d, J=6.7 Hz, 6H), 1.28 (d, J=7.4 Hz, 3H), 1.54 (d, J=6.7 Hz, 3H), 1.30-2.30 (m, 13H), 2.55-2.60 (m, 1H), 2.75-2.91 (m, 3H), 3.26-3.32 (m, 1H), 3.44 (s, 3H), 3.50-3.57 (m, 1H), 4.00 (d, J=11.4 Hz, 1H), 4.17-4.30 (m, 2H), 5.48-5.56 (m, 1H), 5.77 (q, J=6.5 Hz, 1H), 6.66 (dd, J=8.0, 1.6 Hz, 1H), 6.88 (d, J=7.6 Hz, 1H), 7.02-7.15 (m, 7H), 7.22 (d, J=7.6 Hz, 1H), 7.95-8.05 (br s, 1H). LCMS (m/z) 651 [M+H], Tr=5.20 min.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered
  3. filtrationthrough filter aid
  4. washthe filter pad was washed with ethyl acetate
  5. customThe filtrate was evaporated
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e64fee68a124d9f96179fe27ef5e502
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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