N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → HCID 69464877, compound

HRID 1247780Notes

Reaction equation

HRID 1247780 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[N:9][N:10]([CH3:13])[C:11]=1[NH2:12].O=C1CCC(=O)N1[O:21][C:22](=O)[CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>O1CCCC1.[Cl-].[Na+].O>[NH2:12][C:11]1[N:10]([CH3:13])[N:9]=[CH:8][C:7]=1[NH:6][C:22](=[O:21])[CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 69464877HCID 69464877, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 4,5-diamino-1-methylpyrazole sulfuric acid salt (305 g) in tetrahydrofuran (3.05 L) was added tert-butyl 2-[(2,5-dioxo-1-pyrrolidinyl)oxyl]-2-oxoethylcarbamate (415 g) under ice-cooling. To the mixture was added diisopropylethylamine (556 ml) dropwise at a temperature below 10° C. The mixture was stirred at room temperature overnight. To the resulting solution were added brine and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (3.0 L). The aqueous layer was extracted with tetrahydrofuran/ethyl acetate=1/1 (3.0 L) twice. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with diisopropyl ether (1.0 L) and dried in vacuo to give tert-butyl 2-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-2-oxoethylcarbamate (307 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate (3.0 L)
  3. extractionThe aqueous layer was extracted with tetrahydrofuran/ethyl acetate=1/1 (3.0 L) twice
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diisopropyl ether (1.0 L)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-fff39ce103034bd3865362945be54bc7
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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