Methanol → HCID 11249688, compound

HRID 132141Notes

Reaction equation

HRID 132141 reaction equation
C([O:8][C:9](=[O:46])[CH2:10][C@H:11]([NH:23][C:24](=[O:45])[C@@H:25]([NH:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=1)[CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=2)[CH2:15][CH2:14]1)C1C=CC=CC=1.CO.[H][H]>[Pd].C1COCC1>[CH:28]1([CH2:27][CH2:26][C@H:25]([NH:34][C:35](=[O:44])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=2)[C:24]([NH:23][C@H:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[CH2:10][C:9]([OH:46])=[O:8])=[O:45])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

6

Reactant 3

HCID 887MethanolHCID 11456379HCID 11456379, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11249688HCID 11249688, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Example 46 (300 mg, 0.476 mmol) was treated with 10% Pd/C (40 mg), MeOH (5 mL) and THF (5 mL). The atmosphere in the reaction was exchanged for hydrogen and the reaction was allowed to stir for 1 h under a balloon of hydrogen. The atmosphere was then exchanged back to nitrogen, the reaction was filtered through a pad of celite and the solvent was removed to afford 244 mg (95%) of a crystalline solid; 1H NMR (DMSO, 400 MHz) δ 0.55-0.88 (m, 2H), 1.00-1.22 (m, 7H), 2.93 (dd, 1H, J1=5.8, J2=13.6), 3.11 (dd, 1H, J1=7.6, J2=13.7), 3.25 (dd, 1H, J1=8.7, J2=17.5), 3.34 (s, 3H), 3.41-3.50 (m, 1H), 3.81 (s, 3H), 4.30-4.41 (m, 1H), 6.71-6.79 (m, 1H), 6.85-6.89 (m, 1H), 7.07-7.12 (m, 1H), 7.37 (dd, 1H, J1=J2=7.8), 7.40-7.48 (m, 2H), 7.98 (d, 1H, J=8.6), 8.32 (d, 1H, J=8.1); HPLC-MS calcd. for C30H38FN3O5 (M+H) 483.3, found 483.5.

Workup

  1. filtrationthe reaction was filtered through a pad of celite
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-998b04ffd2284a1691280d1c1ad7b80b
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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