(S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Base Information

• Chemical Name: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
• CAS No.: 204317-99-7
• Molecular Formula: C₂₅H₂₁NO₄
• Molecular Weight: 399.446
• European Community (EC) Number: 840-670-9
• DSSTox Substance ID: DTXSID50460377
• Wikidata: Q82284405
• Mol file: 204317-99-7.mol

Synonyms:204317-99-7;Fmoc-L-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;(1S)-2-(9H-fluoren-9-ylmethoxycarbonyl)-3,4-dihydro-1H-isoquinoline-1-carboxylic acid;Fmoc-L-Tic-OH;(1S)-2-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;SCHEMBL800088;DTXSID50460377;AGSTVRGPOSEJQQ-QHCPKHFHSA-N;MFCD03788062;AKOS027323251;BS-42153;CS-0147333;E70672;EN300-179184;J-013313;Fmoc-L-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, AldrichCPR;(1S)-2-(9-fluorenylmethoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid;(1S)-2-(9H-fluoren-9-ylmethoxycarbonyl)-3, 4-dihydro-1H-isoquinoline-1-carboxylic acid;(1S)-3,4-Dihydro-1,2(1H)-isoquinolinedicarboxylic acid 2-(9H-fluoren-9-ylmethyl) ester;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylicacid;1,2(1H)-Isoquinolinedicarboxylic acid, 3,4-dihydro-, 2-(9h-fluoren-9-ylmethyl) ester, (1s)-

Chemical Property of (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Chemical Property:

• Boiling Point: 629.0±55.0 °C(Predicted)
• PKA: 3.43±0.20(Predicted)
• PSA: 66.84000
• Density: 1.324±0.06 g/cm3(Predicted)
• LogP: 4.55740
• Storage Temp.: Store at 0-5°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 399.14705815
• Heavy Atom Count: 30
• Complexity: 629

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-L-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN(C(C2=CC=CC=C21)C(=O)O)C(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Isomeric SMILES: C1CN([C@@H](C2=CC=CC=C21)C(=O)O)C(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

Technology Process of (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

There total 1 articles about (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 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:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-2-((S)-2-Amino-propionyl)-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid → (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (204317-99-7)

Guidance literature:

DOI:10.1055/s-2003-37118

Reference yield:

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (204317-99-7) → (S,E)-N-(3-amino-1H-indazol-6-yl)-2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamide

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; trichlorophosphate / dichloromethane / 0.75 h / Cooling with ice

2: hydrazine hydrate / ethanol / 0.18 h / 160 °C / Microwave irradiation

3: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide; ethyl acetate / 1 h / Cooling with ice

With pyridine; hydrazine hydrate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.7b01171

Reference yield:

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (204317-99-7) → C31H28ClFN6O4

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 1 h / Cooling with ice

2: morpholine / N,N-dimethyl-formamide / 0.5 h

3: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide; ethyl acetate / 1 h / Cooling with ice

With morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.7b01171

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

(S,Z)-4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)-2-fluoroacryloyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoic acid

(S,E)-3-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoic acid

(S,E)-methyl 4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)phenylcarbamate

(S,E)-methyl 4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzylcarbamate

Refernces