2-Methylbenzenesulfonic acid → HCID 86616136, compound

HRID 2266872Notes

Reaction equation

HRID 2266872 reaction equation
C([C@@H](NS(C1C=CC(C)=CC=1)=O)[C@H](C)CC(F)(F)F)#N.[F:21][C:22]([F:32])([F:31])[CH2:23][C@@H:24]([CH3:30])[C@@H:25]([C:27]([OH:29])=[O:28])[NH2:26].[NH4+].[Cl-:34].C1(C)C(S(O)(=O)=O)=CC=CC=1>Cl>[ClH:34].[F:21][C:22]([F:31])([F:32])[CH2:23][C@@H:24]([CH3:30])[C@@H:25]([C:27]([OH:29])=[O:28])[NH2:26]

Participants

6

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 25517Ammonium ChlorideHCID 68428479HCID 68428479, compoundHCID 86594487769169-13-3

Product 1

HCID 86616136HCID 86616136, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of N-[(1S,2R)-1-cyano-4,4,4-trifluoro-2-methylbutyl]-4-methylbenzenesulfinamide (2.34 g, 7.69 mmol) in concentrated hydrochloric acid (75 mL) was heated to reflux for 18.5 h. After cooling to 25° C., the reaction mixture was washed with diethyl ether several times. The aqueous layer was concentrated to give a mixture of 5,5,5-trifluoro-L-alloisoleucine, NH4Cl, and toluenesulfonic acid (2.35 g). The crude amino acid was used in the next step without further purification. Mass spectrum (−ESI): 309 (M−H)−.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18.5 h
  3. washthe reaction mixture was washed with diethyl ether several times
  4. concentrationThe aqueous layer was concentrated
  5. customto give
  6. customThe crude amino acid was used in the next step without further purification

Sources & evidence

ORD record
ord-2e3353d20580430ebcc507cf4e50c8a6
Source dataset
uspto-grants-2010_12
Patent number
US07858658B2

Reaction notes

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