Trifluoroacetic acid → (R)-2-amino-1-((S)-2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-3-hydroxy-3-methylbutan-1-one

HRID 1423147Notes

Reaction equation

HRID 1423147 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:22]=2)[CH2:17][C@@H:16]1[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:14])[C:9]([OH:12])([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@H:8]([C:9]([OH:12])([CH3:10])[CH3:11])[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[CH:22]=2)[CH2:17][C@@H:16]1[CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67291777{(R)-1-[(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carbonyl]-2-hydroxy-2-methyl-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 52918656(R)-2-amino-1-((S)-2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-3-hydroxy-3-methylbutan-1-oneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(R)-1-[(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carbonyl]-2-hydroxy-2-methyl-propyl}-carbamic acid tert-butyl ester intermediate in CH2Cl2 (1 mL) at 0-5° C. was treated with trifluoroacetic acid and stirred at room temperature for 8 hr. After this time the reaction mixture was evaporated and the residue partitioned between EtOAc (5 ml) and a saturated aqueous solution of NaHCO3 (5 mL). The organic extract was further washed with brine then dried over MgSO4, filtered, and evaporated to afford the title compound as an oil (69 mg, 83%). LC/MS (Method B) 2.97 min, [M+1]+ 482.

Workup

  1. customAfter this time the reaction mixture was evaporated
  2. customthe residue partitioned between EtOAc (5 ml)
  3. extractionThe organic extract
  4. washwas further washed with brine
  5. dry with materialthen dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8aae08df49f849149b94d8c24f11a405
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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