Boc-Hyp-OH Chemical Properties

Melting point:

123-127 °C(lit.)

alpha 

-78 º (in H2O)

Boiling point:

390.9±42.0 °C(Predicted)

Density 

1.312±0.06 g/cm3(Predicted)

refractive index 

-68 ° (C=1, MeOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

3.80±0.40(Predicted)

color 

White to off-white

optical activity

[α]20/D 53.5±2°, c = 1% in DMF

Water Solubility 

very faint turbidity

BRN 

4295484

Major Application

peptide synthesis

InChI

1S/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7+/m1/s1

InChIKey

BENKAPCDIOILGV-RQJHMYQMSA-N

SMILES

CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(O)=O

CAS DataBase Reference

13726-69-7(CAS DataBase Reference)

EPA Substance Registry System

(2S,4R)-1-tert-Butyl 4-hydroxy-1,2-pyrrolidinecarboxylate (13726-69-7)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2933 99 80

HazardClass 

IRRITANT

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

Boc-Hyp-OH Usage And Synthesis

Chemical Properties

White powder

Uses

Boc-Hyp-OH is used in the preparation of hydroxyproline derivatives. It is an intermediate in the synthesis of Fosinopril-d5 Sodium Salt (F727803), the labeled analogue of Fosinopril Sodium Salt (F727800), a phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor. Antihypertensive.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Biological Activity

Boc-Hyp-OH is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). It is also a alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs.

Synthesis

1. 18.1g L-proline, 10ml water was added to the reaction flask and stirred. Add 16g of sodium hydroxide configured 0.1 mol/L alkaline solution adjusted to alkaline. Then 8g of (Boc)2O was added to react for I hour,then 8g of (Boc)2O was added to react for I hour and finally 9g of (Boc)2O was added to react for 3 hours.

2. The impurities were extracted three times with petroleum ether 1 ml/time. 3 mol/L hydrochloric acid was used to adjust PH=3 and then the product was extracted three times with ethyl acetate 0.5L/time. Combine the ester layers and wash with brine to neutral. Add 15 g of anhydrous sodium sulfate to dry for 6 hours.

3. Filter, filtrate concentrated dry under reduced pressure, add 50ml petroleum ether stirring crystallization. Centrifuged out the product and dried. Get product 26.3g. yield 93.57%.

IC 50

Non-cleavable Linker

Boc-Hyp-OH(13726-69-7)Related Product Information

• L-Hydroxyproline
• BOC-D-PHE-OSU
• Boc-D-Valine
• 1-BOC-D-PYROGLUTAMIC ACID ETHYL ESTER
• Methyl N-(tert-butoxycarbonyl)-L-threoninate
• Boc-L-serine methyl ester
• BOC-GUANIDINE
• BOC-L-HYDROXYPROLINE METHYL ESTER,(2S,4R)-BOC 4-HYDROXYPROLINE METHYL ESTER,BOC-HYP-OME / BOC-L-HYDROXYPROLINE METHYL ESTER
• BOC-HYP(BZL)-OH
• 1-Boc-L-hydroxyproline ethyl ester
• N-Boc-trans-4-tosyloxy-L-proline methyl ester
• (2S, 4R)-BOC-GAMMA-MSO-PROLINE METHYL ESTER
• Boc-Hyp-OH
• BOC-CIS-HYDROXYPROLINE-OME
• L-Proline
• (2S,4R)-BOC-4-(2-NAPHTHYLMETHOXY)-PYRROLIDINE-2-CARBOXYLIC ACID
• BOC-HYP-OH DCHA
• (2S,4R)-BOC-4-(2-NAPHTHYLOXY)-PYRROLIDINE-2-CARBOXYLIC ACID