N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide

Base Information

• Chemical Name: N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide
• CAS No.: 133230-58-7
• Molecular Formula: C₂₈H₃₇N₃O₇
• Molecular Weight: 527.618
• Mol file: 133230-58-7.mol

Synonyms:

Chemical Property of N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide

There total 9 articles about N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide 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: 54.0%

N-(Boc-Asp(OBn))-α-allylphenylalaninamide (133230-56-5,133230-57-6,141436-28-4) → N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide (133230-58-7,133230-59-8,141436-29-5)

Guidance literature:

With bis(cyclohexanyl)borane; dihydrogen peroxide; In tetrahydrofuran; 2 h at 0 deg C, r.t. overnight;

DOI:10.1021/jo00012a022

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide (133230-58-7,133230-59-8,141436-29-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / triethylamine / dimethylformamide / 0 deg C and than r.t. overnight

2: 76 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / Heating; azeotropic removal of water

3: triethylamine, phosgene / acetonitrile; toluene / 2 h / 0 °C

4: concd. NH₄OH / tetrahydrofuran / Ambient temperature

5: saturated aqueous Ba(OH)2 / methanol / Ambient temperature

6: 3 N HCl / methanol / Ambient temperature

7: 67 percent / N-methylmorpholine, isobutyl chloroformate / CH₂Cl₂ / Ambient temperature

8: 54 percent / dicyclohexylborane, H₂O₂ / tetrahydrofuran / 2 h at 0 deg C, r.t. overnight

With 4-methyl-morpholine; hydrogenchloride; phosgene; barium dihydroxide; ammonium hydroxide; bis(cyclohexanyl)borane; dihydrogen peroxide; toluene-4-sulfonic acid; triethylamine; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00012a022

Reference yield:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → N-(Boc-Asp(OBn))-α-(3-hydroxy-n-propyl)phenylalaninamide (133230-58-7,133230-59-8,141436-29-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / N-methylmorpholine, isobutyl chloroformate / CH₂Cl₂ / Ambient temperature

2: 54 percent / dicyclohexylborane, H₂O₂ / tetrahydrofuran / 2 h at 0 deg C, r.t. overnight

With 4-methyl-morpholine; bis(cyclohexanyl)borane; dihydrogen peroxide; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00012a022

upstream raw materials:

N-(Boc-Asp(OBn))-α-allylphenylalaninamide

L-phenylalanine

BOC-L-aspartic acid 4-benzyl ester

N-trifluoroacetyl-L-phenylalanine

Downstream raw materials:

N-(Boc-Asp(OBn))-α-benzylprolinamide