Trifluoroacetic acid → HCID 131718823, compound

HRID 2257925Notes

Reaction equation

HRID 2257925 reaction equation
C([C@@:3]12[N:10]([C:11](=[O:37])[CH:12]([NH:25][C:26](=[O:36])[C:27]3[CH:32]=[CH:31][C:30]([CH:33]=[N:34][NH2:35])=[CH:29][CH:28]=3)[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20]C(C)(C)C)=[CH:16][CH:15]=3)[CH:7]([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2)C.FC(F)(F)C(O)=O>>[NH2:35][N:34]=[CH:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]([NH:25][CH:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)[C:11]([N:10]2[CH:7]3[CH2:8][CH2:9][C@@H:3]2[CH2:4][CH2:5][CH2:6]3)=[O:37])=[O:36])=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131718824HCID 131718824, compound

Product 1

HCID 131718823HCID 131718823, compoundYield 60%

Procedure

A solution of 150 mg of ethyl (S)-8-[2-(4-aminoiminomethyl-benzoylamino)-3-(4-t-butoxyphenyl)propionyl]-8-azabicyclo[3.2.1]octan-endo-3-yloxyacetate hydrochloride is stirred at room temperature in 5 ml of CH2C2 and 2.5 ml of trifluoroacetic acid and evaporated. With ether the residue gives crystals which are filtered off under suction and dissolved in 5 ml of EtOH. 40 mg of NaOH dissolved in 1 ml of water are added to the solution and the mixture is stirred at room temperature. The reaction solution is neutralized with 1N hydrochloric acid and evaporated. Chromatography of the residue on silica gel RP-18 with water/THF gives 75 mg of (S)-8-[2-(4-aminoiminomethyl-benzoylamino)-3-(4-hydroxyphenyl)propionyl]-8-azabicyclo[3.2.1]octan-endo-3-yloxyacetic acid, MS: 495 (M+H)+.

Workup

  1. customevaporated
  2. customWith ether the residue gives crystals which
  3. filtrationare filtered off under suction
  4. dissolutiondissolved in 5 ml of EtOH
  5. dissolution40 mg of NaOH dissolved in 1 ml of water
  6. additionare added to the solution
  7. customevaporated

Sources & evidence

ORD record
ord-701f32f45069481db1a8fdedcb80905e
Source dataset
uspto-grants-1997_08
Patent number
US05658928

Reaction notes

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