(R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester
• CAS No.: 146398-01-8
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 146398-01-8.mol

Synonyms:(R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

Chemical Property of (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

There total 2 articles about (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester 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: 92.3%

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid (71449-08-6) → (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester (146398-01-8)

Guidance literature:

(R)-2-(((benzyloxy)carbonyl)amino)-4-(tertbutoxy)-4-oxobutanoic acid; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -10 ℃; for 0.5h;

With methanol; sodium tetrahydroborate; In tetrahydrofuran; at -30 ℃; for 1h; Temperature;

Reference yield:

(R)-3-Benzyloxycarbonylamino-4-ethoxycarbonyloxy-4-oxo-butyric acid tert-butyl ester → (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester (146398-01-8)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; for 4h; Yield given; Ambient temperature;

DOI:10.1055/s-1992-26315

Reference yield: 97.0%

methanesulfonyl chloride (124-63-0) + (R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester (146398-01-8) → 3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester (761435-43-2)

Guidance literature:

With TEA; In dichloromethane;

DOI:10.1016/j.bmcl.2004.06.049

upstream raw materials:

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid

Downstream raw materials:

tert-butyl 3-<(benzyloxycarbonyl)amino>-4-(O-tosyl)butanoate

(R)-4-oxo-3-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester

(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid tert-butyl ester