HCID 131735534, compound → HCID 178501303, compound

HRID 522410Notes

Reaction equation

HRID 522410 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[CH2:48][N:23]([C:24](=[O:47])[C@H:25]([CH:38]4[CH2:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[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:49]([O:51][CH3:52])=[O:50])[CH2:21]3)C1C=CC=CC=1>CO.C1COCC1.[Pd].C(OCC)(=O)C>[CH2:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:46][CH:38]1[C@H:25]1[C:24](=[O:47])[N:23]2[CH2:48][C@@H:20]([CH2:21][C@H:22]2[C:49]([O:51][CH3:52])=[O:50])[O:19][C:11]2=[N:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]([OH:8])=[C:10]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]2[CH2:36][C@H:29]2[O:28][C:27](=[O:37])[NH:26]1

Participants

6

Reactant 1

HCID 131735534HCID 131735534, compound

Product 1

HCID 178501303HCID 178501303, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of step 4 (480 mg, 0.686 mmol) in MeOH (9146 μl) and THF (4573 μl) was treated with a catalytic amount of 10% palladium on carbon (36 mg). The mixture was hydrogenated at 20 psi. After 2 hours LCMS showed >70% conversion. Hydrogenation was continued for another 2 h. LCMS showed >90% conversion. The mixture was diluted with ethyl acetate (50 mL) and the solids were removed by filtration. The filtrate was concentrated in rotavap and the residue was purified on a RediSep® (80 g) silica gel column (gradient: 0 to 50% ethyl acetate in hexanes) to give the title compound (420 mg, 0.684 mmol, 100% yield) as a white powder.

Workup

  1. waitHydrogenation was continued for another 2 h
  2. customthe solids were removed by filtration
  3. concentrationThe filtrate was concentrated in rotavap
  4. customthe residue was purified on a RediSep® (80 g) silica gel column (gradient: 0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2d21f61c69284efab2edd83976ec593e
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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