Triethylamine → 2-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate

HRID 459617Notes

Reaction equation

HRID 459617 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(O)(O)(=O)=O.[CH3:30][N:31]1[C:35]([NH2:36])=[C:34]([NH2:37])[CH:33]=[N:32]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>O>[NH2:36][C:35]1[N:31]([CH3:30])[N:32]=[CH:33][C:34]=1[NH:37][C:13](=[O:15])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756240L-N-Cbz-3-N-Boc-Amino-alanineHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 865978712-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamateYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoic acid (1.695 g) and 1-methyl-1H-pyrazole-4,5-diamine sulfate (1.05 g) in water (16 ml) were added triethylamine (1.4 ml) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.73 g). The mixture was stirred at room temperature for 2 hours. The resulting suspension was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 2-benzyl 1-tert-butyl {(2S)-3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxo-1,2-propanediyl}biscarbamate (1.78 g) as a solid.

Workup

  1. extractionThe resulting suspension was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a741ffa55af24e959b6013c00659832b
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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