Trifluoroacetic acid → 4-[(S)-4-Carboxy-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-naphthalene-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid butyl ester

HRID 1185509Notes

Reaction equation

HRID 1185509 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:55])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([O:38][CH2:39][C:40]([N:42]3[CH2:46][CH2:45][CH2:44][C@H:43]3[C:47](=[O:53])[NH:48][CH:49]3[CH2:52][CH2:51][CH2:50]3)=[O:41])[C:35]3[C:30](=[CH:31][C:32]([CH3:54])=[CH:33][CH:34]=3)[CH:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:55])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([O:38][CH2:39][C:40]([N:42]3[CH2:46][CH2:45][CH2:44][C@H:43]3[C:47](=[O:53])[NH:48][CH:49]3[CH2:52][CH2:51][CH2:50]3)=[O:41])[C:35]3[C:30](=[CH:31][C:32]([CH3:54])=[CH:33][CH:34]=3)[CH:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 685969714-[(S)-4-tert-Butoxycarbonyl-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-naphthalene-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid butyl ester

Product 1

HCID 685976274-[(S)-4-Carboxy-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-naphthalene-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.5 g 4-[(S)-4-tert-Butoxycarbonyl-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-naphthalene-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid butyl ester in 10 ml dichloromethane were added 1.1 g TFA. After 3 h stirring at RT the solvents were removed and the residue was codistilled twice with toluene. The crude product was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). Yield: 970 mg MS (ES+): m/e=708.

Workup

  1. customwere removed
  2. customThe crude product was purified by preparative HPLC (
  3. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)

Sources & evidence

ORD record
ord-d0cbc3b5bd1041c7843ba7f8688b7f3e
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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