N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → 7-[2-(Tert-butoxycarbonylamino)acetyl]amino-2,3-dihydro-1h-imidazo[1,2-b]pyrazole

HRID 1247797Notes

Reaction equation

HRID 1247797 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:11]=[N:10][N:9]2[CH2:12][CH2:13][NH:14][C:8]=12.C(N(C(C)C)C(C)C)C.[C:24]([O:28][C:29]([NH:31][CH2:32][C:33](ON1C(=O)CCC1=O)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[C:24]([O:28][C:29]([NH:31][CH2:32][C:33]([NH:6][C:7]1[CH:11]=[N:10][N:9]2[CH2:12][CH2:13][NH:14][C:8]=12)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 81531DiisopropylethylamineHCID 1358007252,3-dihydro-1H-imidazo[1,2-b]pyrazol-7-amine sulfate

Product 1

HCID 1358007307-[2-(Tert-butoxycarbonylamino)acetyl]amino-2,3-dihydro-1h-imidazo[1,2-b]pyrazoleYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazole sulfuric acid salt (1.42 g) and N-ethyldiisopropylamine (2.73 g) in methylene chloride (50 ml) was added N-[2-(tert-butoxycarbonylamino)acetoxy]succinimide (1.90 g). The mixture was stirred at room temperature for 22 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The oily residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform to give 7-[2-(tert-butoxycarbonylamino)acetyl]amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazole (1.07 g) as a solid.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-40184e3c41ff4f22818621079f21b59d
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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