Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-4,5-dihydroxy-pentanoyl]-piperazine-1-carboxylic acid ethyl ester

HRID 1970500Notes

Reaction equation

HRID 1970500 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:52])[C@@H:13]([NH:22][C:23]([C:25]2[CH:29]=[C:28]([O:30][CH2:31][C:32]([N:34]3[CH2:38][CH2:37][CH2:36][C@H:35]3[C:39](=[O:45])[NH:40][CH:41]3[CH2:44][CH2:43][CH2:42]3)=[O:33])[N:27]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:26]=2)=[O:24])[CH2:14][CH:15]2[CH2:19][O:18]C(C)(C)[O:16]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:52])[C@@H:13]([NH:22][C:23]([C:25]2[CH:29]=[C:28]([O:30][CH2:31][C:32]([N:34]3[CH2:38][CH2:37][CH2:36][C@H:35]3[C:39](=[O:45])[NH:40][CH:41]3[CH2:42][CH2:43][CH2:44]3)=[O:33])[N:27]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:26]=2)=[O:24])[CH2:14][CH:15]([OH:16])[CH2:19][OH:18])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 668550964-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 668561924-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-4,5-dihydroxy-pentanoyl]-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 15 mg 4-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propionyl]-piperazine-1-carboxylic acid ethyl ester in 5 ml MeOH were added 5 mg pyridinium p-toluenesulfonate and the solution was stirred for 2 h before being concentrated in vacuo. The residue thus obtained was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were lyophilized to yield the pure product.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe residue thus obtained
  3. customwas purified by preparative HPLC (
  4. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  5. additionThe fractions containing the product
  6. customto yield the pure product

Sources & evidence

ORD record
ord-7d1b74b73fa24a60a2533aaea40b716a
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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