Triethylamine → HCID 86594562, compound

HRID 1744101Notes

Reaction equation

HRID 1744101 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[N:11][S:12][C:13]=1[NH:14][C@H:15]([C:20]([OH:22])=O)[CH2:16][CH:17]([CH3:19])[CH3:18].Cl.[NH2:24][CH2:25][C:26]#[N:27].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C=O.O>[Br:8][C:9]1[CH:10]=[N:11][S:12][C:13]=1[NH:14][C@H:15]([C:20]([NH:27][CH2:26][C:25]#[N:24])=[O:22])[CH2:16][CH:17]([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69152959HCID 69152959, compound

Product 1

HCID 86594562HCID 86594562, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.16 mL, 1.1 mmol) was added dropwise to a solution of N-(4-bromoisothiazol-5-yl)leucine (92 mg, 0.31 mmol), aminoacetonitrile hydrochloride (58 mg, 0.63 mmol) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (180 mg, 0.35 mmol) in N, N-dimethylformamide (1.0 mL) at 0° C. After stirring at rt for 3 h, the reaction vessel contents were poured into water and extracted with a 1:1 mixture of ether and ethyl acetate (3×). The combined extracts were washed with saturated sodium bicarbonate solution, then with saturated sodium chloride solution, and dried (Na2SO4). Concentration under reduced pressure and flash chromatography of the residue on silica gel eluting with a mixture of ethyl acetate and hexanes (2:3) afforded 91 mg of N2-(4-bromoisothiazol-5-yl)-N1-(cyanomethyl)leucinamide as a colorless foam.

Workup

  1. extractionextracted with a 1:1 mixture of ether and ethyl acetate (3×)
  2. washThe combined extracts were washed with saturated sodium bicarbonate solution
  3. dry with materialwith saturated sodium chloride solution, and dried (Na2SO4)
  4. concentrationConcentration under reduced pressure and flash chromatography of the residue on silica gel eluting
  5. additionwith a mixture of ethyl acetate and hexanes (2:3)

Sources & evidence

ORD record
ord-2bcdfe61072b4cceb9a4e57c2d6ab2f0
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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