HCID 131718824, compound → HCID 131718823, compound

HRID 1289106Notes

Reaction equation

HRID 1289106 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 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. 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 1 ml of water
  6. additionare added to the solution
  7. customevaporated

Sources & evidence

ORD record
ord-b429b1d9df6840328085556f6de5f68b
Source dataset
uspto-grants-1998_05
Patent number
US05747522

Reaction notes

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