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CAS No.: | 29133-55-9 |
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Name: | L-Prolinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-histidyl- |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C16H25N5O4 |
Molecular Weight: | 351.406 |
Synonyms: | L-Prolinamide,N-[(1,1-dimethylethoxy)carbonyl]-L-histidyl;Boc-His-Pro-NH2;tert-Butyl ((S)-1-((S)-2-carbamoylpyrrolidin-1-yl)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)carbamate; |
PSA: | 130.41000 |
LogP: | 1.35090 |
N-(tert-butoxycarbonyl)-L-histidine
L-prolinamide
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
Conditions | Yield |
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Stage #1: N-(tert-butoxycarbonyl)-L-histidine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 2h; Stage #2: L-prolinamide In N,N-dimethyl-formamide at 25℃; for 18h; | 73% |
Stage #1: N-(tert-butoxycarbonyl)-L-histidine With HONB; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 0.25h; Stage #2: L-prolinamide In N,N-dimethyl-formamide at 20℃; |
L-prolinamide hydrochloride
N(α)-t-butoxycarbonyl-2,5-dibromo-L-histidine
A
N(α)-t-butoxycarbonyl-D-histidyl-L-prolineamide
B
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
Conditions | Yield |
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With palladium on activated charcoal; Rh on carbon; Amberlite IR 45 (acetate form); hydrogen; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 0 deg C, 4 h, 2.) aq. AcOH, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
L-prolinamide hydrochloride
N(α)-t-butoxycarbonyl-2,5-di-iodo-L-histidine
A
N(α)-t-butoxycarbonyl-D-histidyl-L-prolineamide
B
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
Conditions | Yield |
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With palladium on activated charcoal; rhodium on CaCO3; hydrogen; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 0 deg C, 4 h, 2.) DMF, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
L-prolinamide hydrochloride
Boc-His(Bzl)-OH
A
N(α)-t-butoxycarbonyl-D-histidyl-L-prolineamide
B
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 0 deg C, 4 h, 2.) aq. AcOH, 72 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
(S)-methyl 2-(tert-butoxycarbonylamino)-3-(2,5-dibromo-1H-imidazol-4-yl)propanoate
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 73 percent / NaOH / methanol / 1 h 2: 1.) DCC, Et3N, 2.) Pd-C, H2, Rh-C, Amberlite IR 45 (acetate form) / 1.) DMF, 0 deg C, 4 h, 2.) aq. AcOH, 2 h View Scheme |
N-(tert-butoxycarbonyl)-L-histidine methyl ester
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 25 percent / Et3N, Br2 / CHCl3 / 0 deg C to room temperature 2: 73 percent / NaOH / methanol / 1 h 3: 1.) DCC, Et3N, 2.) Pd-C, H2, Rh-C, Amberlite IR 45 (acetate form) / 1.) DMF, 0 deg C, 4 h, 2.) aq. AcOH, 2 h View Scheme |
trifluoroacetic acid
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
trifluoroacetate salt of L-histidyl-L-prolinamide
Conditions | Yield |
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In dichloromethane at 0℃; for 1h; |
N(α)-t-butoxycarbonyl-L-histidyl-L-prolineamide
Conditions | Yield |
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With hydrogenchloride In methanol |