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13726-69-7

Basic Information
CAS No.: 13726-69-7
Name: Boc-L-Hydroxyproline
Article Data: 100
Cas Database
Molecular Structure:
Molecular Structure of 13726-69-7 (Boc-L-Hydroxyproline)
Formula: C10H17NO5
Molecular Weight: 231.249
Synonyms: Boc-trans-4-hydroxy-L-proline;4-Hydroxy-Pyrrolidine-1,2-Dicarboxylic Acid 1-tert-Butyl Ester;Boc-L-4-hydroxyproline;N-Boc-L-hydroxyproline;(2S,4R)-N-alpha-t-butoxycarbonyl-4-hydroxypyrrolidine-2-car boxylic acid;Boc-4-hydroxy-L-proline;Boc-L-Hyp-OH;Boc-(2S,4R)-hydroxyproline;
EINECS: 604-011-7
Density: 1.312 g/cm3
Melting Point: 123-127 °C(lit.)
Boiling Point: 390.9 °C at 760 mmHg
Flash Point: 190.2 °C
Solubility: very faint turbidity
Safety: 22-24/25
PSA: 87.07000
LogP: 0.37920
Synthetic route
24424-99-5

di-tert-butyl dicarbonate

51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 50℃; for 1h;100%
In tetrahydrofuran; water at 20℃; for 12h;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃;100%
4N-sodium hydroxide

4N-sodium hydroxide

24424-99-5

di-tert-butyl dicarbonate

51-35-4, 913000-57-4

4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; ethyl acetate96%
74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 20℃; for 1h;58%
With sodium hydroxide In tetrahydrofuran at 0℃; for 19h;
Stage #1: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate With water; sodium hydroxide In methanol for 4h;
Stage #2: With citric acid In methanol; water pH=3; Product distribution / selectivity;
Stage #1: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate With methanol; water; lithium hydroxide at 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; acetonitrile for 0.166667h; Cooling with ice bath; Inert atmosphere;
34619-03-9

tert-butyldicarbonate

51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;97%
With sodium hydroxide In water; tert-butyl alcohol at 20℃; for 16h;89%
With sodium hydrogencarbonate In water
51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
In water95%
184046-78-4

(2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate With water; sodium hydroxide In methanol for 6h;
Stage #2: With citric acid In methanol; water pH=3;

potassium hydrogen sulphate

24424-99-5

di-tert-butyl dicarbonate

51-35-4, 913000-57-4

4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
51-35-4, 913000-57-4

4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
3236-56-4

dipercarbonate de O,O-t-butyle

51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; ammonium chloride In tetrahydrofuran; water
115352-39-1, 124662-61-9, 110339-26-9

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: hydrogen / Pd/CaCO3 / ethyl acetate
2: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C
3: hydrazine / ethanol / 6 h / Heating
4: Et3N / CH2Cl2
5: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
6: Et3N / CH2Cl2
7: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
8: K2CO3 / methanol
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    Product Name: Boc-L-Hydroxyproline CAS: 13726-69-7 MF: C10H17NO5 MW: 231.25 EINECS: 604-011-7 Mol File: 13726-69-7.mol Boc-L-Hydroxyproline Structure Boc-L-Hydroxyproline Chemical Properties Melting point 123-127 °C(lit.)

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Chemistry

Molecular structure of Boc-L-Hydroxyproline (CAS NO.13726-69-7) is:

Product Name: Boc-L-Hydroxyproline
CAS Registry Number: 13726-69-7
IUPAC Name: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
Molecular Weight: 231.24568 [g/mol]
Molecular Formula: C10H17NO5
XLogP3-AA: 0.3
H-Bond Donor: 2
H-Bond Acceptor: 5
Melting Point: 123-127 °C(lit.)
Surface Tension: 57 dyne/cm
Density: 1.312 g/cm3
Flash Point: 190.2 °C
Enthalpy of Vaporization: 74.05 kJ/mol
Boiling Point: 390.9 °C at 760 mmHg
Vapour Pressure: 9.99E-08 mmHg at 25°C
Product Categories: Aminoacids derivatives;Pyrrole&Pyrrolidine&Pyrroline;Amino Acids;Hydroxyproline [Hyp];Unusual Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series

Safety Profile

Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
HazardClass: IRRITANT

Specification

 Boc-L-Hydroxyproline , its cas register number is 13726-69-7. It also can be called trans-N-(tert-Butoxycarbonyl)-4-hydroxy-L-proline ; Boc-Hyp-OH ; (2S,4R)-1-tert-Butyl 4-hydroxy-1,2-pyrrolidinecarboxylate ; 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) ester, (2S,4R)- .