(S)-tert-butyl 3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxylate → (R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide

HRID 594822Notes

Reaction equation

HRID 594822 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([C@H:13]([C:27]([NH:29][C:30]3[S:31][C:32]([F:35])=[CH:33][N:34]=3)=[O:28])[CH2:14][C@H:15]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1>Cl>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([C@@H:13]([CH2:14][C@H:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)[C:27]([NH:29][C:30]3[S:31][C:32]([F:35])=[CH:33][N:34]=3)=[O:28])=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 73506951(S)-tert-butyl 3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxylate

Product 1

HCID 118268346(R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamideYield 108.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The (S)-tert-butyl 3-((R)-2-(4-(cyclopropylsulfonyl)phenyl)-3-((5-fluorothiazol-2-yl)amino)-3-oxopropyl)pyrrolidine-1-carboxylate (2.57 g, 4.91 mmol) obtained in Example 1 was dissolved in hydrochloric acid (4 M ethyl acetate solution, 10 mL), and the obtained mixture was then stirred for 10 minutes. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then dissolved in chloroform. The obtained solution was washed with a saturated aqueous solution of sodium hydrogen carbonate, was then dried over sodium sulfate, and was then concentrated in vacuo, so as to obtain (R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide (2.26 g, quant) in the form of a white solid.

Workup

  1. concentrationThereafter, the reaction solution was concentrated in vacuo
  2. dissolutionthe obtained residue was then dissolved in chloroform
  3. washThe obtained solution was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialwas then dried over sodium sulfate
  5. concentrationwas then concentrated in vacuo

Sources & evidence

ORD record
ord-756aa8ca2bc64aa089e280ef8856ba8d
Source dataset
uspto-grants-2016_01
Patent number
US09242978B2

Reaction notes

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