Hydrochloric Acid → (2S,4S)-ethyl 2-amino-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methylhexanoate

HRID 660373Notes

Reaction equation

HRID 660373 reaction equation
[CH2:1]([O:3][C:4]1[C@H:5]([CH2:16][C@@H:17]([CH:33]([CH3:35])[CH3:34])[CH2:18][C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][N:25]3[CH2:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:21][CH:20]=2)[N:6]=C(OCC)[C@@H](C(C)C)N=1)[CH3:2].Cl.C([O-])(O)=[O:38].[Na+]>CC#N>[NH2:6][C@@H:5]([CH2:16][C@H:17]([CH2:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[N:24][N:25]2[CH2:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:21][CH:20]=1)[CH:33]([CH3:35])[CH3:34])[C:4]([O:3][CH2:1][CH3:2])=[O:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 687852626-((S)-2-(((2S,5R)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazin-2-yl)methyl)-3-methylbutyl)-1-(3-methoxypropyl)-1H-indazole

Product 1

HCID 70308734(2S,4S)-ethyl 2-amino-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methylhexanoateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 6-((S)-2-(((2S,5R)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazin-2-yl)methyl)-3-methylbutyl)-1-(3-methoxypropyl)-1H-indazole (300 mg, 0.62 mmol) in CH3CN (5 mL) was added 1 N aq HCl (5 mL) at rt. The mixture was stirred for 5 h, poured into ice-cold, satd aq NaHCO3 and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to give (2S,4S)-ethyl 2-amino-4-((1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-5-methylhexanoate (220 mg, 95%).

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-eec73623eabb46aebd9472cd8ab8b8d9
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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