Descarboxymethyl treprostinil

Base Information

• Chemical Name: Descarboxymethyl treprostinil
• CAS No.: 101692-02-8
• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.483
• UNII: I3U17TZJ64
• Mol file: 101692-02-8.mol

Synonyms:101692-02-8;Descarboxymethyl treprostinil;(1R,2R,3aS,9aS)-1-((S)-3-Hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol;(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-2,5-diol;I3U17TZJ64;(1R,2R,3aS,9aS)-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[g]naphthalene-2,5-diol;(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-L-((3S)-3-hydroxyoctyl)-1H-benz(f)inden-2,5-diol;1H-Benz(f)indene-2,5-diol, 2,3,3a,4,9,9a-hexahydro-1-((3S)-3-hydroxyoctyl)-, (1R,2R,3aS,9aS)-;(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-((3S)-3-hydroxyoctyl)-1H-benz[f]indene-2,5-diol;UNII-I3U17TZJ64;SCHEMBL433054;UTGPMEMKMRVGNE-HUTLKBDOSA-N;AMY21976;F52929;A908155;(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol

Chemical Property of Descarboxymethyl treprostinil

Chemical Property:

• Melting Point: 113-115 °C
• Boiling Point: 506.1±50.0 °C(Predicted)
• PKA: 10.34±0.60(Predicted)
• Density: 1.106±0.06 g/cm3(Predicted)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 332.23514488
• Heavy Atom Count: 24
• Complexity: 385

Purity/Quality:

98%,99%, ^*data from raw suppliers

DescarboxymethylTreprostinil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CCC1C(CC2C1CC3=C(C2)C(=CC=C3)O)O)O
• Isomeric SMILES: CCCCC[C@@H](CC[C@H]1[C@@H](C[C@H]2[C@@H]1CC3=C(C2)C(=CC=C3)O)O)O
• Uses: Descarboxymethyl Treprostinil is an impurity in the synthesis of Treprostinil (T719500), Synthetic analog of Prostacyclin (P839060). Antihypertensive. Treprostinil, marketed under the trade name Remodulin is a medication used to treat pulmonary arterial hypertension (PAH).

Technology Process of Descarboxymethyl treprostinil

There total 112 articles about Descarboxymethyl treprostinil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(1R,2R,3aS,9aS)-1-[(3S)-3-hydroxyoctyl]-5-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol (101692-01-7) → (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8)

Guidance literature:

With aluminum (III) chloride; 1-dodecylthiol; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

Reference yield: 85.0%

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate (1425937-56-9) → (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1h;

Reference yield: 77.0%

(1R,2R,3aS,9aS)-2-((tert-butyldiphenylsilyl)oxy)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-ol (1613271-23-0) → (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 - 50 ℃; for 25.5h; Reagent/catalyst; Temperature; Inert atmosphere;

upstream raw materials:

(1R,2R,3aS,9aS)-1-[(3S)-3-hydroxyoctyl]-5-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol

3-methoxybenzyl alcohol

(2-allyl-3-methoxyphenyl)methanol

3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol

Downstream raw materials:

treprostinil

2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid ethyl ester

2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester

Refernces

• 1、 -. "Process for Preparing Treprostinil and Intermediate Therefor". Paragraph 0188-0190. . Retrieved 2018/02/21.
• 2、 -. "NOVEL INTERMEDIATE FOR SYNTHESIZING TREPROSTINIL DIETHANOLAMINE AND METHOD FOR PREPARING THE SAME". Paragraph 0059; 0073; 0074. . Retrieved 2016/06/28.