2-Methylbenzenesulfonic acid → HCID 86616136, compound

HRID 1985928Notes

Reaction equation

HRID 1985928 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 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 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-f5a2c5ebf61d485686bba8ff2be5d804
Source dataset
uspto-grants-2009_06
Patent number
US07547725B2

Reaction notes

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