N-tert-Butoxycarbonyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide → trans-4-((R)-2-Hydroxy-4-Phenylbutrylamino)-L-Proline 3-Quinolylamide

HRID 2185405Notes

Reaction equation

HRID 2185405 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:38])[C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:19](=[O:30])[C@H:20]([OH:29])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][N:14]2C(OC(C)(C)C)=O)[CH:2]=1>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:38])[C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:19](=[O:30])[C@H:20]([OH:29])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][NH:14]2)[CH:2]=1

Participants

4

Reactant 1

HCID 70173053N-tert-Butoxycarbonyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

Product 1

HCID 59895122trans-4-((R)-2-Hydroxy-4-Phenylbutrylamino)-L-Proline 3-QuinolylamideYield 71%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-tert-butoxycarbonyl-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (1.55 g) was dissolved in trifluoroacetic acid (10 mL)-chloroform (20 mL). After stirring for 1 hr, the reaction mixture was evaporated in vacuo. The residue was diluted with chloroform, and washed with saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (888 mg) as a colorless foam.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionThe residue was diluted with chloroform
  3. washwashed with saturated sodium hydrogen carbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-75017593f79b4093853b36bb87b6f2ed
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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