4-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester → 4-{(S)-4-tert-butoxycarbonyl-2-[(6-isopropyl-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

HRID 553828Notes

Reaction equation

HRID 553828 reaction equation
[CH:1]([Mg]Br)([CH3:3])[CH3:2].[CH2:6]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:44])[C@@H:18]([NH:28][C:29]([C:31]2[CH:36]=[C:35](Cl)[N:34]=[C:33]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:32]=2)=[O:30])[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][CH2:12]1)=[O:10])[CH3:7]>C1COCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[CH2:6]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:44])[C@@H:18]([NH:28][C:29]([C:31]2[CH:36]=[C:35]([CH:1]([CH3:3])[CH3:2])[N:34]=[C:33]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:32]=2)=[O:30])[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][CH2:12]1)=[O:10])[CH3:7]

Participants

5

Reactant 2

HCID 866224044-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl esterHCID 178418365HCID 178418365, compound

Product 1

HCID 674645444-{(S)-4-tert-butoxycarbonyl-2-[(6-isopropyl-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl esterYield 88.1%

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Isopropylmagnesium bromide (29.5 mg) was added to an orange solution of 4-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (56 mg) and iron(III) acetylacetonate (1.8 mg) in anhydrous THF (1 ml) under argon. After stirring at RT for 30 min, it was quenched with a 1M HCl solution and extracted with EA. The org. phases were dried (Na2SO4) and evaporated off to give 50 mg of the desired compound.

Workup

  1. customit was quenched with a 1M HCl solution
  2. extractionextracted with EA
  3. dry with materialphases were dried (Na2SO4)
  4. customevaporated off

Sources & evidence

ORD record
ord-03d00a36f06740ce950467ccd4dfd017
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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