Diisopropylethylamine → HCID 58911823, compound

HRID 1639521Notes

Reaction equation

HRID 1639521 reaction equation
Cl.[NH2:2][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].[C:12]([N:29]=[C:30]=[S:31])([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13].C(N(C(C)C)C(C)C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:5][C:4]1[S:31][C:30]([NH:29][C:12]([O:14][CH2:15][CH:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3[C:28]2=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:13])=[N:2][C:3]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2723717Amino(phenyl)acetonitrile--hydrogen chloride (1/1)HCID 4154759Fmoc isothiocyanate

Product 1

HCID 58911823HCID 58911823, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of α-aminophenylacetonitrile hydrochloride (3.19 g, 18.9 mmol) and Fmoc-isothiocyanate (5.31 g, 18.9 mmol) in DCM was treated with ethyldiisopropylamine (3.62 ml, 20.8 mmol) at 0° C. for 1 hr and then at ambient temperature for 3 hr. The mixture was poured into saturated aqueous sodium bicarbonate and extracted three times into ethyl acetate. The combined organic phases were washed with water and brine, and dried over sodium sulfate and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 5-amino-2-(Fmoc-amino)-4-phenylthiazole (3.75 g, 48%).

Workup

  1. extractionextracted three times into ethyl acetate
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37143c90f5964c4bb78a2c7b3c36423d
Source dataset
uspto-grants-2012_02
Patent number
US08110568B2

Reaction notes

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