Hydrochloric Acid → HCID 20726819, compound

HRID 460463Notes

Reaction equation

HRID 460463 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:46]=[CH:45][C:7]2[N:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([F:44])([F:43])[C:39]([F:42])([F:41])[F:40])[C:28]([O:30]CC)=[O:29])[C@H:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH2:10][O:11][C:6]=2[CH:5]=1.Cl.C(OCC)(=O)C.CCCCCC>C(O)C>[OH:3][C:4]1[CH:46]=[CH:45][C:7]2[N:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([F:44])([F:43])[C:39]([F:40])([F:41])[F:42])[C:28]([OH:30])=[O:29])[C@H:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20726822HCID 20726822, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 20726819HCID 20726819, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Aqueous sodium hydroxide (1N, 1 ml) was added to ethyl 10-[(R)-7-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-benzo[1,4]-oxazine-4-yl]-2-(6,6,7,7,7-pentafluoroheptyl)decanoate (56.8 mg, 0.0902 mmol) in ethanol (1 ml) under a nitrogen stream, followed by stirring for 7 hours at 50° C. After cooling, the reaction mixture was acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1, v/v) to give 10-[(R)-7-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-benzo[1,4]-oxazine-4-yl]-2-(6,6,7,7,7-pentafluoroheptyl)decanoic acid (41.4 mg, Yield 76%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-7125470e247747e986d18f3d69798bf8
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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