4-Toluenesulfonyl chloride → ethyl 7-(N-benzyloxycarbonylamino)-3-p-toluenesulfonyloxy-2-phenylheptanoate

HRID 2392933Notes

Reaction equation

HRID 2392933 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:29])[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[C:39]1([CH3:49])[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([O:29][S:45]([C:42]1[CH:43]=[CH:44][C:39]([CH3:49])=[CH:40][CH:41]=1)(=[O:47])=[O:46])[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 18980744ethyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate

Product 1

HCID 18980751ethyl 7-(N-benzyloxycarbonylamino)-3-p-toluenesulfonyloxy-2-phenylheptanoateYield 47.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

3.5 g (8.6 mmol) of ethyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate obtained in Example 9 was dissolved in 28 ml of pyridine. 240 mg (1.96 mmol) of dimethylaminopyridine was added to the mixture. The mixture was cooled at 0° C. in an ice bath. 2.5 g (13 mmol) of p-toluenesulfonyl chloride was added for 5 minutes, which was stirred for one hour at a same temperature and further stirred at room temperature for 48 hours. After the consumption of the raw material was confirmed by means of HPLC, 100 ml of ethylacetate was added and 2N hydrochloric acid were further added to the reaction mixture to adjust the pH to 4 to extract. A saturated sodium bicarbonate solution was added to the organic layer prepared to neutralize. The neutralized organic layer was washed with saturated brine and then deied with magnesium sulfate anhydride. After the organic layer was concentrated under reduced pressure, the residue was purified by means of SGIC (eluent: hexane/ethylacetate=3/1) to obtain the target compound as a pale yellow oil in an amount 2.3 g at a yield of 47.6%. The analytical results on the target compound are given below.

Workup

  1. stirringfurther stirred at room temperature for 48 hours
  2. customAfter the consumption of the raw material
  3. additionwas added
  4. addition2N hydrochloric acid were further added to the reaction mixture
  5. extractionto extract
  6. additionA saturated sodium bicarbonate solution was added to the organic layer
  7. customprepared
  8. washThe neutralized organic layer was washed with saturated brine
  9. concentrationAfter the organic layer was concentrated under reduced pressure
  10. customthe residue was purified by means of SGIC (eluent: hexane/ethylacetate=3/1)

Sources & evidence

ORD record
ord-41c1b87919124a7182cd721ecd2b2351
Source dataset
uspto-grants-1998_09
Patent number
US05801271

Reaction notes

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