ChemicalBook > CAS DataBase List > (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid

(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid

Product Name
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid
CAS No.
135042-12-5
Chemical Name
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid
Synonyms
BOC-D-CISHYP-OH;Boc-cis-D-Hyp-OH;cis-Boc-D-Hyp-OH;N-Boc-D-cis-Hyp-OH;N-Boc-cis-D-Hyp-OH;ATTERCOP-CHM AT700573;Boc-cis-4-hydroxy-D-proL;BOC-CIS-4-HYDROXY-D-PROLINE;N-BOC-CIS-6-HYDROXY-D-PROLINE;N-BOC-CIS-4-HYDROXY-D-PROLINE
CBNumber
CB4141253
Molecular Formula
C10H17NO5
Formula Weight
231.25
MOL File
135042-12-5.mol
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(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid Property

Melting point:
146-151 °C
alpha 
+48～+52°(c=0.67,MeOH,24℃)
Boiling point:
390.9±42.0 °C(Predicted)
Density 
1.312
storage temp. 
2-8°C
pka
3.80±0.40(Predicted)
form 
powder to crystal
color 
White to Light yellow
optical activity
[α]22/D +50.0°, c = 1 in methanol
InChIKey
BENKAPCDIOILGV-RNFRBKRXSA-N
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Safety

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
706574
Product name
N-Boc-cis-4-hydroxy-D-proline
Purity
97%
Packaging
1g
Price
$74.5
Updated
2023/06/20
TCI Chemical
Product number
B5886
Product name
cis-N-(tert-Butoxycarbonyl)-4-hydroxy-D-proline
Packaging
1G
Price
$31
Updated
2025/07/31
TCI Chemical
Product number
B5886
Product name
cis-N-(tert-Butoxycarbonyl)-4-hydroxy-D-proline
Packaging
5G
Price
$86
Updated
2025/07/31
TRC
Product number
H945705
Product name
(2R,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylicAcid1-(1,1-Dimethylethyl)Ester
Packaging
250mg
Price
$50
Updated
2021/12/16
TRC
Product number
H945705
Product name
(2R,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylicAcid1-(1,1-Dimethylethyl)Ester
Packaging
2.5g
Price
$75
Updated
2021/12/16
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(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid Chemical Properties,Usage,Production

Chemical Properties

White solid

Uses

N-Boc-cis-4-hydroxy-D-proline can be used:

  • As a starting material in the synthesis of DNA mimicking pyrrolidine peptide nucleic acid (PNA) analog.
  • In the synthesis of biologically important macrocyclic dilactones.
  • As an intermediate in the synthesis of histamine H3?receptor antagonists.

Synthesis

24424-99-5

77449-94-6

135042-12-5

(2R,4R)-4-Hydroxypyrrolidine-2-carboxylic acid hydrochloride (0.50 g, 3.0 mmol) was dissolved in 6 mL of THF/H2O (2:1) mixed solvent, followed by the addition of 10% NaOH aqueous solution (1.25 mL) for neutralization. Next, di-tert-butyl dicarbonate (0.95 g, 4.42 mmol) was added to the reaction system. The reaction mixture was stirred at room temperature overnight and then the THF was removed by rotary evaporator.The residue was adjusted to pH 2 with 10% aqueous KHSO4 solution and then extracted with ethyl acetate several times. The organic phases were combined, washed sequentially with water and saturated saline and dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure to give (2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (542 mg, 78%) as a slurry, which was used directly in the next step of the reaction. [α]D25 = +15.3 (c 1.02, MeOH). IR (thin film method): νmax 3462, 2976, 2934, 1740, 1639 cm?1. 1H NMR (400 MHz, CDCl3) δ 7.22 (br s, 1H), 5.11-5.09 (m, 2H), 4.94-4.93 (m, 1H) , 4.40 (s, 1H), 3.64-3.62 (m, 1H), 3.49-3.44 (m, 2H), 2.27-1.90 (s, 9H).13C NMR (100 MHz, CDCl3) δ 172.47, 151.74, 75.81, 67.15, 55.24, 52.27, 35.97, 25.63 ppm. HRMS (ESI): m/z [M + H]+ calcd for C10H18NO5 232.1185; found 232.1171.

IC 50

Non-cleavable Linker

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 681 - 694
[2] Journal of the American Chemical Society, 2013, vol. 135, # 11, p. 4333 - 4363
[3] Tetrahedron Asymmetry, 2015, vol. 26, # 20, p. 1156 - 1166
[4] Patent: TW2017/8221, 2017, A. Location in patent: Page/Page column 92; 93

(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid Suppliers

Americas 1 Canada 1 China 193 Europe 1 France 1 Germany 1 India 3 Japan 3 United Kingdom 2 United States 22 Global 228
J & K SCIENTIFIC LTD.
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View Lastest Price from (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid manufacturers

Honest Joy Holdings Limited
Product
N-Boc-cis-4-hydroxy-D-proline 135042-12-5
Price
US $0.00/KG
Min. Order
1KG
Purity
99.5%
Supply Ability
100 tons
Release date
2022-01-25
Zhuozhou Wenxi import and Export Co., Ltd
Product
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid 135042-12-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
(2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid 135042-12-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09

135042-12-5, (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acidRelated Search:

tert-Butyl peroxyacetate OXALIC ACID 4-Hydroxybenzoic acid Salicylic acid L-PROLINE-(4-3H(N)) BOC-L-Proline 2,3,4-Trihydroxybenzoic acid trans-4-Hydroxy-D-proline tert-Butanol Ethyl 2-(Chlorosulfonyl)acetate 2'-Hydroxy-3-phenylpropiophenone Folic acid cis-4-Hydroxy-L-proline BUTYL OLEATE Buprofezin Butyl acetate Cyhalofop-butyl Citric acid

  • (2R,4R)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
  • BOC-(2R,4R)-(+)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
  • BOC-CIS-4-HYDROXY-D-PROLINE
  • BOC-D-CISHYP-OH
  • N-T-BOC-CIS-4-HYDROXY-D-PROLINE
  • N-BOC-CIS-4-HYDROXY-D-PROLINE
  • N-ALPHA-BUTOXYCARBONYL-CIS-4-HYDROXY-D-PROLINE
  • N-BOC-CIS-6-HYDROXY-D-PROLINE
  • (2r,4r)-n-boc-4-hydroxypyrrolidine-2-carboxylic acid
  • (2R,4R)-N-BOC-4-HYDROXY-D-PROLINE
  • (2R,4R)-1-tert-Butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid
  • (2R,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
  • (2R,4R)-N-Boc-4-hydroxy-2-pyrrolidinecarboxylic acid
  • ATTERCOP-CHM AT700573
  • (4R)-1-(tert-Butoxycarbonyl)-4-hydroxy-D-proline
  • 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-diMethylethyl) ester, (2R-cis)-
  • Boc-cis-D-Hyp-OH
  • cis-Boc-D-Hyp-OH
  • N-Boc-D-cis-Hyp-OH
  • 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-diMethylethyl) ester, (2R,4R)-
  • (Tert-Butoxy)Carbonyl cis-D-Hyp-OH
  • cis-N-Boc-4-hydroxy-D-proline
  • N-Boc-cis-4-hydroxy-D-proline 95+%
  • (2R,4R)N-Boc-trans-4-hydroxy-D-proline
  • (2R,4R)-N-Boc-cis-4-hydroxy-D-proline
  • N-Boc-cis-D-Hyp-OH
  • cis-N-(tert-Butoxycarbonyl)-4-hydroxy-D-proline
  • Boc-cis-4-hydroxy-D-proL
  • (2R,4R)-N-Boc-4-hydroxypyrrolidine-2-carboxylic acid USP/EP/BP
  • N-α-(t-Butoxycarbonyl)-cis-4-hydroxy-D-proline
  • 1-(1,1-Dimethylethyl) (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
  • <i>N</i>-Boc-<i>cis</i>-4-hydroxy-<sc>D</sc>-proline
  • N-Boc-cis-4-hydroxy-D-proline, 97%
  • (2R,4R)-1-BOC-4-Hydroxy-pyrrolidine-2-carboxylic acid
  • 135042-12-5
  • C10H17NO7