N-{[4-(sulfooxy)phenyl]acetyl}-L-norleucylglycyl-L-tryptophyl-N-{(2S)-2-[(N-methyl-L-alpha-aspartyl)amino]-3-phenylpropanoyl}-L-norleucinamide

Base Information

• Chemical Name: N-{[4-(sulfooxy)phenyl]acetyl}-L-norleucylglycyl-L-tryptophyl-N-{(2S)-2-[(N-methyl-L-alpha-aspartyl)amino]-3-phenylpropanoyl}-L-norleucinamide
• CAS No.: 152548-39-5
• Molecular Formula: C₄₇H₆₀N₈O₁₃S
• Molecular Weight: 977.105
• Mol file: 152548-39-5.mol

Synonyms:L-Phenylalaninamide,N-[[4-(sulfooxy)phenyl]acetyl]-L-norleucylglycyl-L-tryptophyl-L-norleucyl-N-methyl-L-a-aspartyl- (9CI); AR-R 15849; ARL15849; ARL 15849XX; FPL 15849

Chemical Property of N-{[4-(sulfooxy)phenyl]acetyl}-L-norleucylglycyl-L-tryptophyl-N-{(2S)-2-[(N-methyl-L-alpha-aspartyl)amino]-3-phenylpropanoyl}-L-norleucinamide

Chemical Property:

• Density: 1.333g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-{[4-(sulfooxy)phenyl]acetyl}-L-norleucylglycyl-L-tryptophyl-N-{(2S)-2-[(N-methyl-L-alpha-aspartyl)amino]-3-phenylpropanoyl}-L-norleucinamide

There total 16 articles about N-{[4-(sulfooxy)phenyl]acetyl}-L-norleucylglycyl-L-tryptophyl-N-{(2S)-2-[(N-methyl-L-alpha-aspartyl)amino]-3-phenylpropanoyl}-L-norleucinamide 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:

Boc-Nle-OH (6404-28-0) → AR-R 15849 (152548-39-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) DIEA, Piv-Cl, 2.) DIEA / 1.) DMF, 15 min, 2.) DMF, RT, 6 h

2: 97 percent / HCl / ethyl acetate / 1 h / -10 - 20 °C

3: 77 percent / DIEA / dimethylformamide / 18 h

4: 51 percent / 1N aq. NaOH / methanol / 1 h / -10 - 20 °C

5: 1.) TBTU, HOBt, DIEA, 2.) DIEA / 1.) DMF, 5 min, 2.) DMF, RT, 2 d

6: 42 percent / H₂ / 10percent Pd/C / methanol / 6 h

7: Pyr*SO₃ / 2.5 h

With hydrogenchloride; sodium hydroxide; hydrogen; sulfur trioxide pyridine complex; pivaloyl chloride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm970477u

Reference yield:

(S)-2-amino-3-phenylpropionamide hydrochloride (65864-22-4) → AR-R 15849 (152548-39-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) DIEA, Piv-Cl, 2.) DIEA / 1.) DMF, 15 min, 2.) DMF, RT, 6 h

2: HCl / ethyl acetate / 1 h / -10 - 20 °C

3: 1.) TBTU, HOBt, DIEA, 2.) DIEA / 1.) DMF, 5 min, 2.) DMF, RT, 2 d

4: HCl / ethyl acetate / 1 h / -10 - 20 °C

5: 1.) TBTU, HOBt, DIEA, 2.) DIEA / 1.) DMF, 5 min, 2.) DMF, RT, 2 d

6: 88 percent / HCl, anisole / ethyl acetate / 1 h / -10 - 20 °C

7: 1.) TBTU, HOBt, DIEA, 2.) DIEA / 1.) DMF, 5 min, 2.) DMF, RT, 2 d

8: 42 percent / H₂ / 10percent Pd/C / methanol / 6 h

9: Pyr*SO₃ / 2.5 h

With hydrogenchloride; hydrogen; sulfur trioxide pyridine complex; pivaloyl chloride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; methoxybenzene; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1021/jm970477u

Reference yield:

(S)-methyl 2-(2-(tert-butoxycarbonylamino)hexanamido)acetate (114516-71-1) → AR-R 15849 (152548-39-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / HCl / ethyl acetate / 1 h / -10 - 20 °C

2: 77 percent / DIEA / dimethylformamide / 18 h

3: 51 percent / 1N aq. NaOH / methanol / 1 h / -10 - 20 °C

4: 1.) TBTU, HOBt, DIEA, 2.) DIEA / 1.) DMF, 5 min, 2.) DMF, RT, 2 d

5: 42 percent / H₂ / 10percent Pd/C / methanol / 6 h

6: Pyr*SO₃ / 2.5 h

With hydrogenchloride; sodium hydroxide; hydrogen; sulfur trioxide pyridine complex; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm970477u

upstream raw materials:

Hpa-Nle-Gly-Trp-Nle-MeAsp-Phe-NH₂

Boc-Nle-OH

(S)-2-amino-3-phenylpropionamide hydrochloride

(S)-methyl 2-(2-(tert-butoxycarbonylamino)hexanamido)acetate