Hydrochloric Acid → toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-methyl-pentyl ester

HRID 1750177Notes

Reaction equation

HRID 1750177 reaction equation
[C:1]([NH:8][C@H:9]([CH2:14][OH:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>C1COCC1.CN(C1C=CN=CC=1)C>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[CH2:14][O:15][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23])=[O:2])([CH3:6])([CH3:5])[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 7018766Boc-L-leucinol

Product 1

HCID 14081313toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-methyl-pentyl esterYield 90.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.50 g of Boc-L-leucinol in 30 ml of THF were added 4.74 g of p-toluenesulfonylchloride, 7.2 ml of TEA and 0.25 g of DMAP. The reaction was stirred at rt overnight. The pH of the reaction was then adjusted to 6 by the addition of 1 M aqueous hydrochloric acid. The phases were separated and the aqueous phase was extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulphate and concentrated to yield 6.94 g of toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-methyl-pentyl ester.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate twice
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9cce5368c8bd4af792beaa84831a8b31
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

Loading…