2-Pyridinemethanamine → HCID 76412589, compound

HRID 1647336Notes

Reaction equation

HRID 1647336 reaction equation
C([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])(C)(C)C.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.CCN(C(C)C)C(C)C>[CH3:11][CH:10]([CH2:12][CH3:13])[CH:9]([NH:8][C:6](=[O:7])[OH:5])[C:14]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:16]

Participants

6

Reactant 3

HCID 195092-PyridinemethanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Product 1

HCID 76412589HCID 76412589, compoundYield 123.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent4×HCID 81531DiisopropylethylamineSolvent

Procedure

To a room temperature solution of 2.33 g of N-(tert-butoxycarbonyl)-L-isoleucine in 5 ml of methylene chloride is added, in the following order, 1.0 g of 2-(aminomethyl)pyridine in 5 ml of methylene chloride, 6.95 g of BOP in 5 ml of methylene chloride and 16 ml of Hunig's base. The reaction is stirred at room temperature for 2 hours, diluted with methylene chloride, and, washed with saturated sodium chloride. The organic layer is dried, filtered and concentrated in vacuo. Purification by chromatography (400 g Silica Gel; 90% ethyl acetate/hexane) gives 3.03 g of the desired product as an oil.

Workup

  1. washwashed with saturated sodium chloride
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (400 g Silica Gel; 90% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-399604af18264ae08cd7b0fc99d5738e
Source dataset
uspto-grants-1995_07
Patent number
US05430150

Reaction notes

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