Trifluoroacetic acid → 2(S)-(L-histidyl)amino-1-cyclohexyl-(S)-hydroxy-6-methylheptane

HRID 1649921Notes

Reaction equation

HRID 1649921 reaction equation
C(OC([NH:8][C@H:9]([C:16]([NH:18][C@H:19]([C@@H:27](O)[CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=[O:37]>C(OCC)(=O)C>[NH2:8][C@H:9]([C:16]([NH:18][C@@H:19]([CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C@@H:20]([OH:37])[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178444654HCID 178444654, compound

Product 1

HCID 1784439352(S)-(L-histidyl)amino-1-cyclohexyl-(S)-hydroxy-6-methylheptane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2(S)-(N-t-butoxycarbonyl-L-histidyl)amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (383 mg) in trifluoroacetic acid (10 ml) was stirred at 0° C. for 30 minutes. After concentration of the mixture in vacuo, the residue was dissolved in ethyl acetate (20 ml). The solution was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo to give 2(S)-(L-histidyl)amino-1-cyclohexyl-(S)-hydroxy-6-methylheptane (275 mg) as an amorphous powder.

Workup

  1. washThe solution was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25ae1cc3e60545f3a5d2f548485cefc4
Source dataset
uspto-grants-1990_05
Patent number
US04921855

Reaction notes

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