Pyridine → 4-[(S)-5-Acetoxy-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-pentanoyl]-piperazine-1-carboxylic acid butyl ester

HRID 1970613Notes

Reaction equation

HRID 1970613 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:50])[C@@H:15]([NH:20][C:21]([C:23]2[CH:27]=[C:26]([O:28][CH2:29][C:30]([N:32]3[CH2:36][CH2:35][CH2:34][C@H:33]3[C:37](=[O:43])[NH:38][CH:39]3[CH2:42][CH2:41][CH2:40]3)=[O:31])[N:25]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:24]=2)=[O:22])[CH2:16][CH2:17][CH2:18][OH:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[C:57](OC(=O)C)(=[O:59])[CH3:58]>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:50])[C@@H:15]([NH:20][C:21]([C:23]2[CH:27]=[C:26]([O:28][CH2:29][C:30]([N:32]3[CH2:36][CH2:35][CH2:34][C@H:33]3[C:37](=[O:43])[NH:38][CH:39]3[CH2:42][CH2:41][CH2:40]3)=[O:31])[N:25]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:24]=2)=[O:22])[CH2:16][CH2:17][CH2:18][O:19][C:57](=[O:59])[CH3:58])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 668547594-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-5-hydroxy-pentanoyl]-piperazine-1-carboxylic acid butyl ester

Product 1

HCID 668545264-[(S)-5-Acetoxy-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-pentanoyl]-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 65 mg 4-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-5-hydroxy-pentanoyl]-piperazine-1-carboxylic acid butyl ester in 4 ml dichloromethane were added 15 l pyridine, 10 l acetic anhydride and a catalytic amount of DMAP. After stirring for 24 h at room temperature the reaction mixture was concentrated and the crude product thus obtained was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA) to give the title compound.

Workup

  1. concentrationwas concentrated
  2. customthe crude product thus obtained
  3. customwas purified by preparative HPLC (
  4. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)

Sources & evidence

ORD record
ord-085e46b94a2b4934a3e222431ca3b9a9
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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