Hydrochloric Acid → (3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)-octanoic Acid Tert-butyl Ester

HRID 130537Notes

Reaction equation

HRID 130537 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][C@@H:8]([CH2:15][OH:16])[CH2:9][C@H:10]([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:25](Cl)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:17])[CH2:7][C@@H:8]([CH2:15][O:16][S:25]([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:9][C@H:10]([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57070108(3S,5R)-3-Hydroxymethyl-5-methyl-octanoic Acid Tert-butyl Ester

Product 1

HCID 57178500(3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)-octanoic Acid Tert-butyl EsterYield 91.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To alcohol 103 (1.98 g, 8.1 mmol) in CH2Cl2 (40 mL) at room temperature was added triethylamine (2.4 g, 0.024 mol), DMAP (20 mg) and tosyl chloride (2.3 g, 0.012 mol). After 14 hours 1N HCl was added and the two layers separated. The aqueous phase was extracted with ether and the combined organic phases dried (MgSO4) and concentrated. Flash chromatography (95% hexane/EtOAc) gave tosylate 104 as an oil (2.94 g, 91%). 13C NMR (100 MHz; CDCl3) 171.60, 144.92, 133.07, 130.02, 128.12, 80.80, 72.15, 39.73, 38.09, 37.89, 32.67, 29.71, 28.22, 21.83, 20.10, 19.54, 14.49.

Workup

  1. customthe two layers separated
  2. extractionThe aqueous phase was extracted with ether
  3. dry with materialthe combined organic phases dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e9f85e9a539942c89ebdd8d7652e17ff
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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