Carbamic acid, [3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

Base Information

• Chemical Name: Carbamic acid, [3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-
• CAS No.: 149598-21-0
• Molecular Formula: C₁₀H₂₁NO₄
• Molecular Weight: 219.281
• Mol file: 149598-21-0.mol

Synonyms:erythro-(2S)-2-tert-Butoxycarbonylamino-3-methyl-1,4-butanediol

Chemical Property of Carbamic acid, [3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

Chemical Property:

• Boiling Point: 370.5±32.0 °C(Predicted)
• PKA: 11.84±0.46(Predicted)
• PSA: 78.79000
• Density: 1.087±0.06 g/cm3(Predicted)
• LogP: 0.89130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

There total 2 articles about Carbamic acid, [3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1- 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:

di-tert-butyl dicarbonate (24424-99-5) + (2S,3R)-2-amino-3-methylbutane-1,4-diol (178899-79-1) → (2S,3R)-2-(tert-butoxycarbonyl)amino-3-methylbutane-1,4-diol (149598-21-0,734548-35-7)

Guidance literature:

In isopropyl alcohol; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.44.1128

Reference yield:

(2S,3R-)-2-[N-Benzyl-N-(9-phenylfluoren-9-yl)]amino-3-methylbutane-1,4-diol (178755-12-9) → (2S,3R)-2-(tert-butoxycarbonyl)amino-3-methylbutane-1,4-diol (149598-21-0,734548-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 5percent Pd/C / methanol / 2 h / 40 °C / 3800 Torr

2: propan-2-ol / 0.5 h / Ambient temperature

With hydrogen; palladium on activated charcoal; In methanol; isopropyl alcohol;

DOI:10.1248/cpb.44.1128

Reference yield:

(2S,3R)-2-(tert-butoxycarbonyl)amino-3-methylbutane-1,4-diol (149598-21-0,734548-35-7) → (3S,4S)-1-benzyl-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine (127199-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NEt₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 71 percent / 72 h / Ambient temperature; var. temp., var,reaction time, var. amounts of reagents

With triethylamine; In dichloromethane;

DOI:10.1248/cpb.44.1128

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3R)-2-amino-3-methylbutane-1,4-diol

(2S,3R-)-2-[N-Benzyl-N-(9-phenylfluoren-9-yl)]amino-3-methylbutane-1,4-diol

Downstream raw materials:

(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine

(3S,4S)-1-benzyl-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine

Refernces

• 1、 Yoshida, Toshihiko,Takeshita, Makoto,Orita, Hitomi,Kado, Noriyuki,Yasuda, Shingo,Kato, Hideo,Itoh, Yasuo. "A large-scale preparation of (3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine and its analogs from L-aspartic acid". . p. 1128 - 1131. Retrieved 2007/10/03.