Triethylamine → HCID 86604875, compound

HRID 1432011Notes

Reaction equation

HRID 1432011 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C@H:11]([CH2:16][C:17]#[CH:18])[C:12](OC)=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].CCN(CC)CC.CCOC(C)=O>CO.O.[Fe]>[CH2:16]([C@@H:11]1[C:12](=[O:13])[NH:1][C:4]2[CH:9]=[CH:8][CH:7]=[N:6][C:5]=2[NH:10]1)[C:17]#[CH:18]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 86604876HCID 86604876, compound

Product 1

HCID 86604875HCID 86604875, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To (R)-methyl 2-(3-nitropyridin-2-ylamino)pent-4-ynoate (2.6 g, 10 mmol) in MeOH (60 mL) was added ammonium chloride (2.8 g, 52 mmol) in water (50 mL) and iron (2.7 g, 48 mmol) and the reaction mixture was heated to reflux for 8 h. The reaction mixture was cooled to room temperature and Et3N (1.3 mL) was added. After 10 h, EtOAc (100 mL) was added and the mixture was stirred for 2 h. The solution was decanted and evaporated. Water (15 mL) was added and the reaction mixture was filtered and washed with water to give colored solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. customThe solution was decanted
  4. customevaporated
  5. additionWater (15 mL) was added
  6. filtrationthe reaction mixture was filtered
  7. washwashed with water
  8. customto give colored solid

Sources & evidence

ORD record
ord-218c83a681c143c1905aa211991e624d
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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