HCID 86726230, compound → HCID 42625640, compound

HRID 1174329Notes

Reaction equation

HRID 1174329 reaction equation
[CH3:1][C:2]([CH3:62])([CH3:61])[C@H:3]([N:45]1[CH2:49][CH2:48][N:47]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([N+:57]([O-])=O)=[CH:53][CH:52]=2)[C:46]1=[O:60])[C:4]([NH:6][C@@H:7]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@@H:8]([OH:37])[CH2:9][C@@H:10]([NH:24][C:25]([C@@H:27]([NH:32][C:33](=[O:36])[O:34][CH3:35])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1)=[O:5]>C(O)C.[Pd]>[NH2:57][C:54]1[CH:55]=[CH:56][C:51]([CH2:50][N:47]2[CH2:48][CH2:49][N:45]([C@@H:3]([C:2]([CH3:62])([CH3:61])[CH3:1])[C:4]([NH:6][C@@H:7]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:8]([OH:37])[CH2:9][C@@H:10]([NH:24][C:25]([C@@H:27]([NH:32][C:33](=[O:36])[O:34][CH3:35])[C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[CH:14][CH:13]=3)=[O:5])[C:46]2=[O:60])=[CH:52][CH:53]=1

Participants

4

Reactant 1

HCID 86726230HCID 86726230, compound

Product 1

HCID 42625640HCID 42625640, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 124B (0.065 g, 0.076 mmol) in ethanol (1.5 mL) was treated with 10% Pd on carbon (0.024 g), stirred under an atmosphere of hydrogen (balloon pressure) at 25° C. for 2.5 hours, filtered concentrated under reduced pressure. The residue was purified by reversed phase chromatography on a C18 column eluting with a gradient starting with 5-100% acetonitrile in water (0.1% TFA). The product was partitioned between ethyl acetate and saturated NaHCO3, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (0.024 g, 39% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.83(s, 9H), 0.87(s, 9H), 1.60-1.48(m, 2H), 2.29-2.20(m, 1H), 2.67-2.53(m, 3H), 2.92-2.75(m, 3H), 3.16-3.08(m, 1H), 3.50(s, 3H), 3.71-3.61(m, 1H), 3.86-3.83(d, J=9.93 Hz, 1H), 4.07(s, 1H), 4.11(s, 2H), 4.23-4.09(m, 2H), 4.56-4.53(d, J=7.72 Hz, 1H), 5.00(s, 2H), 6.55-6.52(d, J=8.46 Hz, 2H), 6.67-6.64(d, J=9.93 Hz, 1H), 6.94-6.91(d, J=8.46 Hz, 2H), 7.10-7.02(m, 5H), 7.23-7.21(d, J=8.46 Hz, 2H), 7.33-7.29(m, 1H), 7.45-7.42(d, J=9.56 Hz, 1H), 7.91-7.82(m, 5H), 8.64-8.62(m, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by reversed phase chromatography on a C18 column
  4. washeluting with a gradient
  5. customThe product was partitioned between ethyl acetate and saturated NaHCO3
  6. washthe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0f53eafac86f45a290dbff5d437daaaf
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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