HCID 118098738, compound → HCID 118098737, compound

HRID 708869Notes

Reaction equation

HRID 708869 reaction equation
C([O:8][C:9]1[C:26]([F:27])=[CH:25][C:24]2=[CH:28][C:10]=1[CH2:11][N:12]([CH3:61])[C:13](=[O:60])[C@H:14]([NH:34][C:35]1[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=1)[C:41]([N:45]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[N:40][CH:39]=[CH:38]3)[C:15]1[CH:32]=[C:31]([CH3:33])[C:18]([C@@H:19]([CH3:30])[CH2:20][O:21][C:22](=[O:29])[NH:23]2)=[CH:17][CH:16]=1)C1C=CC=CC=1>CO.[Pd]>[C:48]([O:47][C:46]([N:45]([C:41]1[C:42]2[C:37](=[CH:36][C:35]([NH:34][C@H:14]3[C:13](=[O:60])[N:12]([CH3:61])[CH2:11][C:10]4[CH:28]=[C:24]([CH:25]=[C:26]([F:27])[C:9]=4[OH:8])[NH:23][C:22](=[O:29])[O:21][CH2:20][C@H:19]([CH3:30])[C:18]4[C:31]([CH3:33])=[CH:32][C:15]3=[CH:16][CH:17]=4)=[CH:44][CH:43]=2)[CH:38]=[CH:39][N:40]=1)[C:53](=[O:54])[O:55][C:56]([CH3:58])([CH3:59])[CH3:57])=[O:52])([CH3:49])([CH3:50])[CH3:51]

Participants

4

Reactant 1

HCID 118098738HCID 118098738, compound

Product 1

HCID 118098737HCID 118098737, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

17I (0.227 g, 0.272 mmol) was dissolved in methanol (10 mL), degassed (3× Ar/vacuum). Then, Pd—C (0.029 g, 0.027 mmol) was added, and the reaction mixture was degassed again (3× Ar/vacuum). The resulting suspension was stirred under hydrogen (1 atm, balloon) for 1 h. The reaction mixture was filtered though a membrane filter, washed with MeOH (2×2 mL). MeOH was removed under reduced pressure to give 17J (0.199 g, 0.268 mmol, 98% yield) as a yellowish glass, which was lyophilized to give as a yellow solid. MS (ESI) m/z: 744.3 [M+1]+. 1H NMR: (400 MHz, CD3OD) δ ppm 8.04 (1H, d, J=5.77 Hz), 7.58-7.69 (2H, m), 7.50 (1H, d, J=6.02 Hz), 7.43 (1H, d, J=7.78 Hz), 7.24-7.30 (2H, m), 6.86 (1H, d, J=2.01 Hz), 6.50 (1H, dd, J=11.29, 2.01 Hz), 5.71 (1H, s), 5.56 (1H, br. s.), 5.36 (1H, d, J=17.32 Hz), 4.67 (1H, t, J=10.92 Hz), 3.86-3.99 (2H, m), 3.65 (2H, s), 3.41-3.55 (1H, m), 3.28 (3H, br. s.), 2.34 (3H, s), 1.23-1.36 (21H, m).

Workup

  1. customdegassed (3× Ar/vacuum)
  2. customthe reaction mixture was degassed again (3× Ar/vacuum)
  3. filtrationThe reaction mixture was filtered though a membrane
  4. filtrationfilter
  5. washwashed with MeOH (2×2 mL)
  6. customMeOH was removed under reduced pressure

Sources & evidence

ORD record
ord-d80c58989cc74a30b907c7f912666c70
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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