(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetate

Base Information

• Chemical Name: (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetate
• CAS No.: 376608-71-8
• Molecular Formula: C9H9F2N.C8H8O3
• Molecular Weight: 321.324
• Hs Code.: 29181990
• European Community (EC) Number: 454-140-6,619-507-9
• UNII: TH0OSF4LF9
• DSSTox Substance ID: DTXSID60433193
• Mol file: 376608-71-8.mol

Synonyms:376608-71-8;(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetate;(1r,2s)-2-(3,4-difluorophenyl)cyclopropanaminium (2r)-hydroxy(phenyl)ethanoate;TH0OSF4LF9;(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate;(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine;(2R)-2-hydroxy-2-phenylacetic acid;(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine R-mandelate;(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetic acid;MFCD21362980;trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine (2R)-2-hydroxy-2-phenylethanoate;EX-7182;UNII-TH0OSF4LF9;DPP-8;C17H17F2NO3;DTXSID60433193;(1R,2S)-2-(3,4-Difluorophenyl) cyclopropanaminium (2R)-hydroxy(phenyl)ethanoat;GUESUQPLVFMJIT-KLTOLQSASA-N;CS-M1881;AKOS022186450;AM85747;AC-27491;AS-51549;EC 454-140-6;P12919;(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine D-Mandelic acid;(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine (2R)-2-hydroxy-2-phenylacetic acid;(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine (2R)-2-hydroxy-2-phenylacetic acid;(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine(R)-2-hydroxy-2-phenylacetate;(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine;(R)-2-hydroxy-2-phenylacetate;(2R)-Hydroxy(phenyl)acetic acid--(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine (1/1);trans-(1R,2S)-2-(3,4-Difluorophenyl-cyclopropanaminium (2R)-2-hydroxy-2-phenylethanoate

Chemical Property of (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetate

Chemical Property:

• PSA: 83.55000
• LogP: 3.28430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 321.11764973
• Heavy Atom Count: 23
• Complexity: 312

Purity/Quality:

98%99% ^*data from raw suppliers

(1R,2S)-2-(3,4-Difluorophenyl)cyclopropan-1-ammonium (2R)-2-hydroxy-2-phenylacetate 97.0% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1N)C2=CC(=C(C=C2)F)F.C1=CC=C(C=C1)C(C(=O)O)O
• Isomeric SMILES: C1[C@H]([C@@H]1N)C2=CC(=C(C=C2)F)F.C1=CC=C(C=C1)[C@H](C(=O)O)O
• Description: (1R, 2R)-2-(3, 4-difluorophenyl) cyclopropanamine(S)-(carboxylato(phenyl)methyl) holmium is a useful pharmacological intermediate. It is utilized as an intermediate of trcagrelor, which is a platelet aggregation inhibitor used for prevention of thrombotic events occurring in people with acute coronary syndrome or myocardial infarction.
• Uses: (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine is an intermediate in the preparation of orally active reversible P2Y12 receptor antagonists for the prevention of thrombosis.

Technology Process of (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetate

There total 27 articles about (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (R)-2-hydroxy-2-phenylacetate 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: 82.0%

trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid (220352-36-3,1006614-50-1) + (R)-Mandelic Acid (611-71-2) → trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt (376608-71-8)

Guidance literature:

trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid; With pyridine; thionyl chloride; In toluene; at 70 ℃; for 4h;

With sodium azide; tetrabutylammomium bromide; sodium carbonate; In water; toluene; at 0 ℃; for 2h;

(R)-Mandelic Acid; In ethyl acetate; at 17 - 25 ℃; for 3h;

Reference yield: 80.0%

(R)-Mandelic Acid (611-71-2) + (1R,2S)-2-(3,4-difluorophenyl)cyclopropyl carboxylic acid (1006614-50-1) → trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt (376608-71-8)

Guidance literature:

(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl carboxylic acid; With chloroformic acid ethyl ester; triethylamine; In water; acetone; for 1h;

(R)-Mandelic Acid; In ethanol; at 20 ℃; for 1h;

Reference yield: 70.1%

(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine (1006614-49-8,220352-38-5,1459719-81-3) + (R)-Mandelic Acid (611-71-2) → trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt (376608-71-8)

Guidance literature:

In Isopropyl acetate; at 0 - 20 ℃; for 4h;

upstream raw materials:

ortho-difluorobenzene

trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane

(R)-Mandelic Acid

3-chloro-1-(3',4'-difluorophenyl)-propan-1-one

Downstream raw materials:

tert-butyl ((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate

[3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol

ticagrelor

tert-butyl (6-chloro-5-nitro-2-(propylthio)pyrimidin-4-yl)((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate

Refernces

• 1、 -. "Preparation method of ticagrelor key intermediate". Paragraph 0014. . Retrieved 2020/05/08.
• 2、 -. "(1 R, 2 S) - 2 - (3, 4 - difluorophenyl) amine ·D - mandelic acid salt preparation method". . . Retrieved 2018/02/04.