Ditert-butyl aziridine-1,2-dicarboxylate

Base Information

• Chemical Name: Ditert-butyl aziridine-1,2-dicarboxylate
• CAS No.: 178602-42-1
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.303
• European Community (EC) Number: 841-980-7
• DSSTox Substance ID: DTXSID20939101
• Nikkaji Number: J3.286.798G
• Mol file: 178602-42-1.mol

Synonyms:127700-62-3;ditert-butyl aziridine-1,2-dicarboxylate;(S)-BIS(TERT-BUTYL) AZIRIDINE-1,2-DICARBOXYLATE;1,2-DI-TERT-BUTYL AZIRIDINE-1,2-DICARBOXYLATE;DTXSID20939101;CFA70062;AKOS015841354;Di-tert-butyl aziridine-1,2-dicarboxylate;EN300-7442834;1,2-Aziridinedicarboxylic acid, 1,2-bis(1,1-dimethylethyl) ester

Chemical Property of Ditert-butyl aziridine-1,2-dicarboxylate

Chemical Property:

• Boiling Point: 291.458 °C at 760 mmHg
• Flash Point: 130.069 °C
• PSA: 55.61000
• Density: 1.113 g/cm³
• LogP: 1.88530
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 243.14705815
• Heavy Atom Count: 17
• Complexity: 324

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-Di-tert-butylaziridine-1,2-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CN1C(=O)OC(C)(C)C

Technology Process of Ditert-butyl aziridine-1,2-dicarboxylate

There total 6 articles about Ditert-butyl aziridine-1,2-dicarboxylate 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: 73.0%

(S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester (126496-79-5) + lithium tert-butoxide (1907-33-1) → di-tert-butyl (S)-aziridine-1,2-dicarboxylate (178602-42-1)

Guidance literature:

In tetrahydrofuran; at -78 - -20 ℃; Inert atmosphere;

DOI:10.1021/ol9024919

Reference yield: 19.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + (S)-2-Boc-aziridine-2-carboxylic acid (1286768-92-0) → di-tert-butyl (S)-aziridine-1,2-dicarboxylate (178602-42-1)

Guidance literature:

With boron trifluoride diethyl etherate; In cyclohexane; acetone; for 12h;

DOI:10.1016/0040-4039(96)00676-4

Reference yield:

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7) → di-tert-butyl (S)-aziridine-1,2-dicarboxylate (178602-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / 4 h / 20 °C / 760 Torr

2: 1.) diethoxytriphenylphosphorane; 2.) DMAP / 1.) toluene, 20-40 degC, 24 h; 2.) MeCN

With dmap; diethoxyltriphenylphosphorane; hydrogen; palladium on activated charcoal;

DOI:10.1016/0040-4039(96)00676-4

upstream raw materials:

tert-Butyl 2,2,2-trichloroacetimidate

(S)-2-Boc-aziridine-2-carboxylic acid

di-tert-butyl dicarbonate

tert-butyl (2S)-2-amino-3-hydroxypropanoate

Downstream raw materials:

C₂₆H₄₁NO₉

(S)-2-[(tert-butoxycarbonyl)amino]heptanoic acid

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

Boc-Nle-OH

Refernces

• 1、 Baldwin, Jack E.,Farthing, Christopher N.,Russell, Andrew T.,Schofield, Christopher J.,Spivey, Alan C.. "Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for α-amino acid synthesis". . p. 3761 - 3764. Retrieved 2007/10/03.