tert-butyl N-(2-hydroxy-3-phenoxypropyl)carbamate

Base Information

• Chemical Name: tert-butyl N-(2-hydroxy-3-phenoxypropyl)carbamate
• CAS No.: 121282-71-1
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.325
• DSSTox Substance ID: DTXSID501199269
• Mol file: 121282-71-1.mol

Synonyms:121282-71-1;tert-butyl N-(2-hydroxy-3-phenoxypropyl)carbamate;SCHEMBL15691093;KKYSYZXSOCQCJG-UHFFFAOYSA-N;DTXSID501199269;EN300-7548532;rac-tert-Butyl (2-hydroxy-3-phenoxypropyl)carbamate;1,1-Dimethylethyl N-(2-hydroxy-3-phenoxypropyl)carbamate

Chemical Property of tert-butyl N-(2-hydroxy-3-phenoxypropyl)carbamate

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 267.14705815
• Heavy Atom Count: 19
• Complexity: 269

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC(COC1=CC=CC=C1)O

Technology Process of tert-butyl N-(2-hydroxy-3-phenoxypropyl)carbamate

There total 4 articles about tert-butyl N-(2-hydroxy-3-phenoxypropyl)carbamate 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-azido-3-phenoxypropan-2-ol (121282-65-3) → rac-1-(N-tert-Butoxycarbonylamino)-2-hydroxy-3-phenoxypropane (121282-71-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 21h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80629-8

Reference yield: 92.2%

tert-butyl N-(2-oxiranylmethyl)carbamate (148982-76-7,149057-20-5,115198-80-6) + phenol (108-95-2,27073-41-2) → rac-1-(N-tert-Butoxycarbonylamino)-2-hydroxy-3-phenoxypropane (121282-71-1)

Guidance literature:

With potassium hydroxide; at 0 - 22 ℃;

DOI:10.1039/b102895m

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → rac-1-(N-tert-Butoxycarbonylamino)-2-hydroxy-3-phenoxypropane (121282-71-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 98.1 percent / Et₃N / CH₂Cl₂

2: 88.3 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 6 h / Heating

3: 92.2 percent / aq. KOH / 0 - 22 °C

With potassium hydroxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1039/b102895m

upstream raw materials:

di-tert-butyl dicarbonate

1-azido-3-phenoxypropan-2-ol

tert-butyl N-(2-oxiranylmethyl)carbamate

phenol

Downstream raw materials:

rac-N-(tert-Butoxycarbonyl)-2-phenoxymethylaziridine

(R)-(-)-N-(tert-Butoxycarbonyl)-2-phenoxymethylaziridine

rac-tert-butyl (2-amino-3-phenoxypropyl)carbamate

rac-1-(N-tert-Butoxycarbonylamino)-2-oxo-3-phenoxypropane