Sodium Hydroxide → HCID 68440062, compound

HRID 2246955Notes

Reaction equation

HRID 2246955 reaction equation
C[O:2][C:3](=[O:49])[C:4]([CH3:48])([CH3:47])[CH2:5][C@@H:6]1[CH2:11][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C@@H:9]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:8][N:7]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38].[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C@@H:10]2[C@@H:9]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:8][N:7]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:38])=[O:39])[C@H:6]([CH2:5][C:4]([CH3:48])([CH3:47])[C:3]([OH:49])=[O:2])[CH2:11]2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68442663HCID 68442663, compound

Product 1

HCID 68440062HCID 68440062, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 8.62 g of 3-[(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-2,2-dimethyl-propionic acid methyl ester in 20 ml tetrahydrofuran and 50 ml ethanol are added 60 ml of a 20% sodium hydroxide solution. The reaction mixture is stirred for 4 hours at 65° C. The organic solvents are evaporated under reduced pressure and the remaining solution is acidified with 6M aqueous hydrochloric acid until pH 2. This mixture is extracted with 200 ml ethyl acetate (3×). The combined organic layers are washed with brine and dried with sodiumsulfate. The organic layer is filtered and evaporated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a colourless foam. Rf=0.27 (EtOAc-heptane 3:1); Rt=5.10.

Workup

  1. customThe organic solvents are evaporated under reduced pressure
  2. extractionThis mixture is extracted with 200 ml ethyl acetate (3×)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried with sodiumsulfate
  5. filtrationThe organic layer is filtered
  6. customevaporated under reduced pressure
  7. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-0bc03f3e0ab440c086ba00789866f57b
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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