HCID 131718824, compound → HCID 131718823, compound

HRID 1077924Notes

Reaction equation

HRID 1077924 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>C(Cl)Cl>[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 1

HCID 131718824HCID 131718824, compound

Product 1

HCID 131718823HCID 131718823, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 CH2Cl2 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 I 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. custom2.5 ml of trifluoroacetic acid and evaporated
  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 I ml of water
  6. additionare added to the solution
  7. customevaporated

Sources & evidence

ORD record
ord-e5c0e99a9f594a79945b6f9f2b9b0b51
Source dataset
uspto-grants-1996_08
Patent number
US05545658

Reaction notes

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