p-Toluenesulfonic acid → HCID 66876645, compound

HRID 1863971Notes

Reaction equation

HRID 1863971 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@@H:15]([CH2:17][O:18]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@H:14]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][O:45][CH2:46][C@@H:47]([CH3:51])[CH2:48][O:49][CH3:50])=[CH:40][CH:39]=2)[C@@H:13]([O:52][CH2:53][C:54]2[CH:55]=[CH:56][C:57]3[O:62][CH2:61][C:60](=[O:63])[N:59]([CH2:64][CH2:65][CH2:66][O:67][CH3:68])[C:58]=3[CH:69]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1.CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][C@H:13]([O:52][CH2:53][C:54]2[CH:55]=[CH:56][C:57]3[O:62][CH2:61][C:60](=[O:63])[N:59]([CH2:64][CH2:65][CH2:66][O:67][CH3:68])[C:58]=3[CH:69]=2)[C@@H:14]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][O:45][CH2:46][C@@H:47]([CH3:51])[CH2:48][O:49][CH3:50])=[CH:40][CH:39]=2)[C@H:15]([CH2:17][OH:18])[CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 86629098HCID 86629098, compound

Product 1

HCID 66876645HCID 66876645, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.526 mmol of (3R,4R,5S)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl) -phenyl]-3-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo [1,4]oxazin-6-ylmethoxy]-5-trityloxymethyl-piperidine-1-carboxylic acid benzyl ester in 20 ml of tetrahydrofuran and 80 ml of methanol is treated with 12.789 mmol of toluene-4-sulfonic acid.monohydrate. After stirring for 15 hours, the reaction mixture is basified with saturated aqueous sodium bicarbonate solution and concentrated under reduced pressure to remove most of the methanol and tetrahydrofuran. The residue is extracted with dichloromethane (3×)—the combined organic layers are washed successively with water and brine, dried with sodium sulfate and evaporated. The title compound is obtained as a yellow oil from the residue by flash chromatography (SiO2 60F). Rt=4.86 (gradient I).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove most of the methanol and tetrahydrofuran
  3. extractionThe residue is extracted with dichloromethane (3×)—the combined organic layers
  4. washare washed successively with water and brine
  5. dry with materialdried with sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-1d6d827b75174b4c80f03f71a1433293
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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