Hydrochloric Acid → HCID 178445930, compound

HRID 1750178Notes

Reaction equation

HRID 1750178 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:10]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[N:32]1[N:33]=[C:34]([SH:37])[NH:35][CH:36]=1.Cl>CC(C)=O.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][S:37][C:34]1[NH:35][CH:36]=[N:32][N:33]=1)[CH2:22][CH:23]([CH3:24])[CH3:25])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14081313toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-methyl-pentyl esterHCID 178527972HCID 178527972, compound

Product 1

HCID 178445930HCID 178445930, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To 250 mg of toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-methyl-pentyl ester in 2.5 ml acetone and 0.5 ml water were added 112 mg of potassium carbonate, followed by the addition of 75 mg 4H-1,2,4-triazole-3-thiol. The reaction was heated in a microwave reactor for 5 min to 100° C. The pH was then adjusted to 7 by the addition of 2 M aqueous hydrochloric acid and the mixture was extracted with ethyl acetate twice. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. 161 mg (80%) of [(S)-3-Methyl-1-(4H-[1,2,4]triazol-3-ylsulfanylmethyl)-butyl]-carbamic acid tert-butyl ester were obtained.

Workup

  1. temperatureThe reaction was heated in a microwave reactor for 5 min to 100° C
  2. extractionthe mixture was extracted with ethyl acetate twice
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f334e48d00c64ca7b139f44e5148edca
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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