Ammonia → Isohexane ethyl acetate

HRID 496634Notes

Reaction equation

HRID 496634 reaction equation
O.O.Cl[Sn]Cl.[CH2:6]([C:13]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:14]=1[C:15]([NH:17][CH:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N.[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36]>>[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36].[CH3:14][CH2:13][CH2:6][CH:7]([CH3:12])[CH3:8].[NH2:31][C:29]1[CH:28]=[CH:27][C:14]([C:15]([NH:17][C@@H:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=[O:20])=[O:16])=[C:13]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:30]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 22321899Methyl 2-[(2-benzyl-4-nitro-benzoyl)amino]-4-methylsulfanyl-butyrate

Product 2

HCID 21882781Isohexane ethyl acetateYield 50%HCID 57043324methyl (2S)-2-(4-amino-2-benzyl-benzoylamino)-4-methylsulfanyl-butyrate

Procedure

SnCl2.2H2O (2.5 g, 11.08 mmol) was added to a stirred solution of compound 30 (2.24 mmol) in ethyl acetate(50 mL) and the resulting mixture heated at reflux for 18 h. The reaction mixture was cooled to ambient temperature and treated with 0.880 SG NH3(aq) dropwise to pH8. The resulting precipitate was removed by filtration through diatomaceous earth (Celite®)(545). The filtrates were then evaporated and purified by chromatography (Mega Bond Elut,Silica), eluting with dichloromethane and then 50% ethyl acetate/i-hexane to give the desired compound 21.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 18 h
  3. customThe resulting precipitate was removed by filtration through diatomaceous earth (Celite®)(545)
  4. customThe filtrates were then evaporated
  5. custompurified by chromatography (Mega Bond Elut,Silica)
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-47d19e01bdea473b823dd75d95e1948a
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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