4-Toluenesulfonyl chloride → HCID 22880591, compound

HRID 1941306Notes

Reaction equation

HRID 1941306 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C@@H:5]([NH:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[C:6]([O:8][CH3:9])=[O:7].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[CH2:14]([O:13][C:11]([NH:10][C@H:5]([CH2:4][CH2:3][NH:2][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])[C:6]([O:8][CH3:9])=[O:7])=[O:12])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 22880592HCID 22880592, compound

Product 1

HCID 22880591HCID 22880591, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 4-amino-2(R)-(N-butyloxycarbonylamino)butyrate hydrochloride (2.28 g, 8.5 mmol) and p-toluenesulfonyl chloride (1.62 g, 8.5 mmol) in 10 mL CHCl3 cooled in an ice bath was added diisopropylethylamine (4.5 mL, 26 mmol). The mixture was stirred at room temperature overnight and concentrated. Ethyl acetate was added and the solution was washed with citric acid, brine, NaHCO3 and brine, dried (MgSO4) and concentrated. Purification on a silica gel column using 40% ethyl acetate/hexane gave 2.16 g (66%) product. 1H-NMR: d (CDCl3) 7.75 (d, 2H ); 7.26 (d, 2H); 5.72 (t, 1H); 5.22 (d, 1H); 4.32 (m, 1H); 3.72 (s, 3H); 3.18 (m, 1H); 2.82 (m, 1H); 2.41 (s, 3H); 2.10 (m, 1H); 1.60 (m, 1H); 1.40 (s, 9H).

Workup

  1. concentrationconcentrated
  2. additionEthyl acetate was added
  3. washthe solution was washed with citric acid, brine, NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification on a silica gel column

Sources & evidence

ORD record
ord-8b8079e5b838421c8cac9f278a8fd583
Source dataset
uspto-grants-1997_12
Patent number
US05703092

Reaction notes

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