HCID 131735533, compound → HCID 178501304, compound

HRID 522407Notes

Reaction equation

HRID 522407 reaction equation
C([O:8][C:9]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=[C:11]2[O:19][C@H:20]3[CH2:46][N:23]([C:24](=[O:45])[C@H:25]([C:38]4([CH3:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[NH:26][C:27](=[O:37])[O:28][C@@H:29]4[CH2:36][C@H:30]4[CH2:31][CH2:32][CH2:33][C:34]#[C:35][C:10]=12)[C@H:22]([C:47]([O:49][CH3:50])=[O:48])[CH2:21]3)C1C=CC=CC=1>CO.C1COCC1.[Pd].ClCCl>[CH3:44][C:38]1([C@H:25]2[C:24](=[O:45])[N:23]3[CH2:46][C@@H:20]([CH2:21][C@H:22]3[C:47]([O:49][CH3:50])=[O:48])[O:19][C:11]3=[N:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:9]([OH:8])=[C:10]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]3[CH2:36][C@H:29]3[O:28][C:27](=[O:37])[NH:26]2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 1

HCID 131735533HCID 131735533, compound

Product 1

HCID 178501304HCID 178501304, compoundYield 93.4%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of step 4 (870 mg, 1.280 mmol) in MeOH (8532 μl) and THF (4266 μl) was treated with a catalytic amount of 10% palladium on carbon (68 mg). The mixture was hydrogenated at 30 psi. After 6 hours LCMS showed complete reaction. The mixture was diluted with dichloromethane (50 mL) and the solids were removed by filtration. The filtrate was concentrated in rotavap and the residue was purified on a gold cap RediSep® (80 g) silica gel column (gradient: 0 to 40% ethyl acetate in hexanes) to give the title compound (710 mg, 1.196 mmol, 93% yield) as a white powder.

Workup

  1. customAfter 6 hours LCMS showed complete reaction
  2. customthe solids were removed by filtration
  3. concentrationThe filtrate was concentrated in rotavap
  4. customthe residue was purified on a gold
  5. customcap RediSep® (80 g) silica gel column (gradient: 0 to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9a8970f9e57a453ea27055155dcc058f
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

Loading…