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159857-79-1

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Basic Information
CAS No.: 159857-79-1
Name: Val-cit-PAB-OH
Molecular Structure:
Molecular Structure of 159857-79-1 (Val-cit-PAB-OH)
Formula: C18H29N5O4
Molecular Weight: 379.459
Synonyms: Val-cit-PAB-OH;L-Valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide;(S)-2-((R)-2-amino-3-methylbutanamido)-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide
EINECS: -0
Density: 1.243±0.06 g/cm3(Predicted)
Melting Point: 168 °C(dec.)
Boiling Point: 715.0±60.0 °C(Predicted)
PSA: 159.57000
LogP: 2.28940
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Synthetic route
159858-22-7

(9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
With diethylamine In N,N-dimethyl-formamide for 24h;100%
With diethylamine In N,N-dimethyl-formamide for 2h;96%
With diethylamine In N,N-dimethyl-formamide for 2h;96%
870487-04-0

(9H-fluoren-9-yl)methyl (S)-(1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate

86060-87-9

Fmoc-Val-OPfp

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Stage #1: (S)-(9H-fluoren-9-yl)methyl (1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)carbamate With piperidine In N,N-dimethyl-formamide at 23℃; for 3h;
Stage #2: Fmoc-Val-OPfp With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 24h;
Stage #3: With piperidine In N,N-dimethyl-formamide at 23℃; for 1h;		93%
68858-20-8

Fmoc-Val-OH

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
2: sodium hydrogencarbonate / water; tetrahydrofuran
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
4: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 3 steps
1.1: dicyclohexyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione / tetrahydrofuran / 16 h / 20 °C
1.2: 16 h / 20 °C
2.1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C
3.1: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: dicyclohexyl-carbodiimide / acetonitrile; tetrahydrofuran / 24 h / 0 - 20 °C
2: sodium hydrogencarbonate / tetrahydrofuran; 1,2-dimethoxyethane; water / 24 h / 20 °C
3: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 48 h / 20 °C / Darkness
4: diethylamine / 24 h / 20 °C
View Scheme
130878-68-1

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / water; tetrahydrofuran
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
3: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 3 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
2: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
159858-21-6

(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
2: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 2 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C / Darkness; Inert atmosphere
2: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
View Scheme
623-04-1

4-aminobenzenemethanol

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide
2: diethylamine / 1-methyl-pyrrolidin-2-one
View Scheme
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 16 h / 20 °C
2.1: diethylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: dichloromethane / 3 h / 20 °C
5.1: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 20 °C
2.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
4.2: 3 h / 20 °C
View Scheme
1037794-22-1

(S)-2-amino-N-(4-(hydroxymethyl)phenyl)-5-ureidopentanamide

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 3 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 16 h / 20 °C
2.1: dichloromethane / 3 h / 20 °C
3.1: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 16 h / 20 °C
2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
2.2: 3 h / 20 °C
View Scheme
1037793-80-8

(S)-tert-butyl 1-(4-(hydroxymethyl)phenylamino)-1-oxo-5-ureidopentan-2-ylcarbamate

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
2: N,N-dimethyl-formamide / 3 h / 20 °C
3: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
372-75-8

Citrulline

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / water; 1,4-dioxane / 2 h / 0 - 20 °C
2: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / methanol; dichloromethane / 16 h / 20 °C / Inert atmosphere
3: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
4: N,N-dimethyl-formamide / 3 h / 20 °C
5: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / 1,2-dimethoxyethane; tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
2: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C / Darkness; Inert atmosphere
3: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 24 h / 20 °C / Inert atmosphere
2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 30 h / 20 °C / Darkness; Inert atmosphere
3: piperidine / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere
4: N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
5: diethylamine / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C / Inert atmosphere
View Scheme

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid

159857-79-1

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / methanol; dichloromethane / 16 h / 20 °C / Inert atmosphere
2: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
3: N,N-dimethyl-formamide / 3 h / 20 °C
4: piperidine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 16 h / 20 °C
2.1: diethylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: dichloromethane / 3 h / 20 °C
5.1: sodium hydroxide; water / 1,4-dioxane / 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 20 °C
2.1: diethylamine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 16 h / 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
4.2: 3 h / 20 °C
View Scheme
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