HCID 86675669, compound → HCID 70913586, compound

HRID 1914504Notes

Reaction equation

HRID 1914504 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH3:38])=[C:33]([CH2:39][C:40]3[CH:49]=[CH:48][C:43]4[O:44][CH2:45][CH2:46][O:47][C:42]=4[CH:41]=3)[CH:32]=2)[O:11][C@@H:10]1[CH2:50][O:51][C:52](=[O:65])[C@H:53]([NH:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH:54]([CH3:56])[CH3:55])C1C=CC=CC=1>C(OCC)(=O)C.CO.[OH-].[Pd+2].[OH-]>[O:44]1[C:43]2[CH:48]=[CH:49][C:40]([CH2:39][C:33]3[CH:32]=[C:31]([C@@H:12]4[O:11][C@H:10]([CH2:50][O:51][C:52](=[O:65])[C@H:53]([NH:57][C:58]([O:60][C:61]([CH3:63])([CH3:62])[CH3:64])=[O:59])[CH:54]([CH3:56])[CH3:55])[C@@H:9]([OH:8])[C@H:14]([OH:15])[C@H:13]4[OH:23])[CH:36]=[CH:35][C:34]=3[CH2:37][CH3:38])=[CH:41][C:42]=2[O:47][CH2:46][CH2:45]1

Participants

4

Reactant 1

HCID 86675669HCID 86675669, compound

Product 1

HCID 70913586HCID 70913586, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a stirred solution of (R)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (2R,3R,4R,5S,65)-3,4,5-tris-benzyloxy-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-tetrahydro-pyran-2-ylmethyl ester (4.5 g, 5.0 mmol) in ethyl acetate: methanol (1:4 mixture, 50 ml) was added palladium hydroxide (2.0 g). After stirring for overnight at room temperature, reaction mixture was filtered through celite bed, concentrated and purified by silica gel column chromatography to give 3.12 g of (R)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester as a white solid.

Workup

  1. customreaction mixture
  2. filtrationwas filtered through celite bed
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-83601210c8c14302a1b0b68ca9acf501
Source dataset
uspto-grants-2013_12
Patent number
US08614195B2

Reaction notes

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