HCID 118045115, compound → HCID 118045267, compound

HRID 2284864Notes

Reaction equation

HRID 2284864 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][O:45]CC4C=CC=CC=4)=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([O:41][CH2:42][CH2:43][CH2:44][OH:45])=[CH:39][CH:40]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 118045115HCID 118045115, compound

Product 1

HCID 118045267HCID 118045267, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a 0.5 L round bottom flask add [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-(3-benzyloxypropoxy)phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (10.34 mmol) and ethyl acetate (80 mL). To this solution add 5% Pd/C pre wet with ethyl acetate (20 mL). While stiffing, vacuum purge the mixture with hydrogen (3×) then stir under hydrogen for 16 hours. Filter through diatomaceous earth and rinse with ethyl acetate (100 mL). Concentrate the filtrate under reduced pressure to give the title compound in sufficient purity to use in the next step (6.5 g): mass spectrum (m/z): 626.4 (M+1).

Workup

  1. customvacuum purge the mixture with hydrogen (3×)
  2. filtrationFilter through diatomaceous earth
  3. washrinse with ethyl acetate (100 mL)
  4. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c01d81ee749a40a787d97f765fdc2009
Source dataset
uspto-grants-2015_09
Patent number
US09145437B2

Reaction notes

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