(R)-N-(tert-Butoxycarbonyl)-2-(1-naphthyl)glycine

Base Information

• Chemical Name: (R)-N-(tert-Butoxycarbonyl)-2-(1-naphthyl)glycine
• CAS No.: 146621-91-2
• Molecular Formula: C₁₇H₁₉NO₄
• Molecular Weight: 301.342
• DSSTox Substance ID: DTXSID501158029
• Nikkaji Number: J870.868A
• Mol file: 146621-91-2.mol

Synonyms:146621-91-2;(R)-2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-1-yl)acetic acid;SCHEMBL5848471;DTXSID501158029;AKOS015910985;(R)-N-(tert-Butoxycarbonyl)-2-(1-naphthyl)glycine;(alphaR)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-naphthaleneacetic acid

Chemical Property of (R)-N-(tert-Butoxycarbonyl)-2-(1-naphthyl)glycine

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 301.13140809
• Heavy Atom Count: 22
• Complexity: 415

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1=CC=CC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C1=CC=CC2=CC=CC=C21)C(=O)O

Technology Process of (R)-N-(tert-Butoxycarbonyl)-2-(1-naphthyl)glycine

There total 10 articles about (R)-N-(tert-Butoxycarbonyl)-2-(1-naphthyl)glycine 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: 90.0%

(+/-)-N-tert-butoxycarbonyl-α-1-naphthylglycine methyl ester (896132-09-5) → 2-(tert-butoxycarbonylamino)-2-(naphthalen-1-yl)acetic acid (146621-91-2,146621-93-4,14675-99-1)

Guidance literature:

(+/-)-N-tert-butoxycarbonyl-α-1-naphthylglycine methyl ester; With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 16h;

With potassium hydrogensulfate; In tetrahydrofuran; water; pH=1;

DOI:10.1016/j.bmc.2012.04.002

Reference yield:

hydroxyimino-[1]naphthyl-acetic acid (37059-68-0) → 2-(tert-butoxycarbonylamino)-2-(naphthalen-1-yl)acetic acid (146621-91-2,146621-93-4,14675-99-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, conc aq. HCl / 5percent Pd/C / ethanol / 6 h / 760 Torr / Ambient temperature

2: 2N aq. NaOH / 2-methyl-propan-2-ol / 24 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; hydrogen; palladium on activated charcoal; In ethanol; tert-butyl alcohol;

DOI:10.1021/jm00055a002

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + C28H45NO2Sn (1291065-85-4) → 2-(tert-butoxycarbonylamino)-2-(naphthalen-1-yl)acetic acid (146621-91-2,146621-93-4,14675-99-1)

Guidance literature:

carbon dioxide; C₂₈H₄₅NO₂Sn; With cesium fluoride; In N,N-dimethyl-formamide; at 100 ℃; for 3h; under 7500.75 Torr; Autoclave;

With hydrogenchloride; In diethyl ether; water; N,N-dimethyl-formamide; at 0 ℃; pH=2; Inert atmosphere;

DOI:10.1021/jo202597p

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

2-amino-2-(naphthalen-1-yl)acetic acid

di-tert-butyl dicarbonate

hydroxyimino-[1]naphthyl-acetic acid

Downstream raw materials:

(RS)-N-benzyl 2-amino-2-(naphthalen-1-yl)acetamide

(RS)-N-benzyl 2-amino-2-(naphthalen-1-yl)acetamide hydrochloride

(RS)-N-benzyl 2-(t-butoxycarbonylamino)-2-(naphthalen-1-yl)acetamide