Water → HCID 86633189, compound

HRID 1160467Notes

Reaction equation

HRID 1160467 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([NH2:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11].C(N(CC)CC)C.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([NH:9][S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[CH2:6][N:5]1[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 70288620HCID 70288620, compound

Product 1

HCID 86633189HCID 86633189, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 3 ml solution of N-α-butoxycarbonyl-trans-4-amino-L-proline methylester 49 mg (0.20 mmol), triethylamine 0.042 ml (0.30 mmol), p-toluenesulfonyl chloride 42 mg (0.22 mmol) in chloroform was stirred at room temperature for 16 hours. To the reaction solution was added water and the mixture was extracted with chloroform and dried on magnesium sulfate. After filtration and concentration of the mixture, the residue was purified by a column chromatography on silica gel (eluted with a mixed solvent of ethyl acetate and hexane) to give 64 mg (0.16 mmol) of the title compound (yield: 80%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customdried on magnesium sulfate
  3. filtrationAfter filtration and concentration of the mixture
  4. customthe residue was purified by a column chromatography on silica gel (
  5. washeluted with a mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-9b837411bd064477b92c9652c63aa340
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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