(2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylic Acid, Methyl Ester

Base Information

• Chemical Name: (2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylic Acid, Methyl Ester
• CAS No.: 145451-90-7
• Molecular Formula: C20H31NO4
• Molecular Weight: 349.47
• DSSTox Substance ID: DTXSID50448599
• Wikidata: Q82267666
• Mol file: 145451-90-7.mol

Synonyms:145451-90-7;(2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylic Acid, Methyl Ester;METHYL (2R,4R)-3-BENZYL-2-TERT-BUTYL-4-[(1S)-1-HYDROXY-2-METHYLPROPYL]-1,3-OXAZOLIDINE-4-CARBOXYLATE;4-Oxazolidinecarboxylic acid, 2-(1,1-dimethylethyl)-4-(1-hydroxy-2-methylpropyl)-3-(phenylmethyl)-, methyl ester, [2R-[2alpha,4alpha,4(S*)]]- (9CI);DTXSID50448599;QCRKOHCZGTXCPI-SQGPQFPESA-N;AKOS030241535;(2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylic Acid, Methyl Es

Chemical Property of (2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylic Acid, Methyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 91-92°C
• Boiling Point: 425.765°C at 760 mmHg
• Flash Point: 211.295°C
• PSA: 59.00000
• Density: 1.099g/cm³
• LogP: 2.75760
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 349.22530847
• Heavy Atom Count: 25
• Complexity: 453

Purity/Quality:

98%Min ^*data from raw suppliers

(2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylicAcid,MethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C1(COC(N1CC2=CC=CC=C2)C(C)(C)C)C(=O)OC)O
• Isomeric SMILES: CC(C)[C@@H]([C@]1(CO[C@@H](N1CC2=CC=CC=C2)C(C)(C)C)C(=O)OC)O

Technology Process of (2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylic Acid, Methyl Ester

There total 1 articles about (2R,4S)-2-t-Butyl-N-benzyl-4-[1-(S)-hydroxy-2-methylpropyl]-oxazolidine-4-carboxylic Acid, Methyl 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: 51.0%

3-Benzyl-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester + isobutyraldehyde (78-84-2) → (2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester (145451-90-7)

Guidance literature:

With lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 8h;

DOI:10.1021/ja00052a096

Reference yield:

(2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester (145451-90-7) → (2S,3S)-2-Benzylamino-3-hydroxy-2-hydroxymethyl-4-methyl-pentanoic acid methyl ester

Guidance literature:

With trifluorormethanesulfonic acid; In methanol; water; at 80 - 85 ℃; for 6.5h;

DOI:10.1021/ja973444c

Reference yield:

(2R,4R)-3-Benzyl-2-tert-butyl-4-((S)-1-hydroxy-2-methyl-propyl)-oxazolidine-4-carboxylic acid methyl ester (145451-90-7) → (1R,4R,5S)-4-Benzyl-1-((S)-1-hydroxy-2-methyl-propyl)-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

Guidance literature:

Multi-step reaction with 11 steps

1: trifluoromethanesulfonic acid / methanol; H₂O / 6.5 h / 80 - 85 °C

2: imidazole / dimethylformamide / 25 h / 23 °C

3: p-TsOH*H₂O / benzene / 0.5 h / 80 °C

4: LiBH₄ / tetrahydrofuran; methanol / 20 h / 23 °C

5: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 2 h / -78 °C

6: 1.) MgI₂, 3.) K₂CO₃

7: 1.) i-Pr₂NEt, H₂ / 1.) 10percent Pd/C / 1.) EtOH, 23 deg C, 22 h, 2.) MeOH, 50 deg C, 24 h

8: 48percent HF / acetonitrile / 24 h / 23 °C

9: Et₃N, oxalyl chloride, DMSO / CH₂Cl₂ / 2 h / -78 °C

10: 1.) NaClO₂, 20percent aq. NaH₂PO₄, 2.) 1,3-propanedithiol, HCl / 1.) t-BuOH, 2-methyl-2-butene, 23 deg C, 1 h, 2.) CF₃CH₂OH, 50-55 deg C, 7.5 h

11: Et₃N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 0.5 h / 23 °C

With 1H-imidazole; 1.3-propanedithiol; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; oxalyl dichloride; trifluorormethanesulfonic acid; hydrogen fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja973444c

upstream raw materials:

isobutyraldehyde

Downstream raw materials:

(2R,3S)-2-Benzylamino-3-hydroxy-2-hydroxymethyl-4-methyl-pentanoic acid methyl ester

[(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidin-4-yl]-methanol

(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde

(4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carboxylic acid methyl ester