Diisopropylethylamine → 2-[(5-Chloro-4-iodo-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

HRID 1480036

Reaction equation

HRID 1480036 reaction equation
[Cl:1][C:2]1[C:3]([I:11])=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[CH3:35][O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[NH2:39].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:35][O:36][C:37](=[O:42])[C:38]([NH:39][C:8]([C:5]1[CH:4]=[C:3]([I:11])[C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 855920915-Chloro-4-iodo-2-pyridinecarboxylic acid

Product 1

HCID 762819992-[(5-Chloro-4-iodo-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-4-iodo-2-pyridinecarboxylic acid (CAN 120643-06-3, 100 mg, 353 μmol) in DMF (2 mL) was added TBTU (170 mg, 529 μmol) and 2-methyl-alanine methyl ester hydrochloride (59.6 mg, 388 μmol) to give a light yellow suspension. DIEA (308 μL, 1.77 mmol) was added and the reaction mixture was stirred for 3 h. The crude reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient) to deliver the desired compound (40.5 mg, 30%) as yellow oil. MS (ESI, m/z): 382.9 (MH+).

Workup

  1. customto give a light yellow suspension
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-b4a35e39ed3b4fe2ab4673e1d777a7ac
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Linked notes

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