L-Norvaline, 4,4-difluoro- (9CI)

Base Information

• Chemical Name: L-Norvaline, 4,4-difluoro- (9CI)
• CAS No.: 148043-97-4
• Molecular Formula: C₅H₉F₂NO₂
• Molecular Weight: 153.129
• Mol file: 148043-97-4.mol

Synonyms:L-Norvaline, 4,4-difluoro- (9CI)

Chemical Property of L-Norvaline, 4,4-difluoro- (9CI)

Chemical Property:

• Melting Point: 230 °C(Solv: chloroform (67-66-3))
• Boiling Point: 225.8±40.0 °C(Predicted)
• PKA: 2.13±0.10(Predicted)
• PSA: 63.32000
• Density: 1.268±0.06 g/cm3(Predicted)
• LogP: 1.14390

Purity/Quality:

99%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Norvaline, 4,4-difluoro- (9CI)

There total 12 articles about L-Norvaline, 4,4-difluoro- (9CI) 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: 81.0%

(S)-2-azido-4,4-difluoropentanoic acid (148043-93-0) → (-)-(S)-4,4-difluoronorvaline (148043-97-4)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; for 23h; under 2068.6 Torr;

Reference yield: 60.0%

(4S)-4-(2,2-difluoropropyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one (774603-48-4) → (-)-(S)-4,4-difluoronorvaline (148043-97-4)

Guidance literature:

With water; In acetonitrile; for 24h; Heating;

DOI:10.1055/s-2004-829131

Reference yield:

ethyl 4,4-difluoropentanoate (659-72-3) → (-)-(S)-4,4-difluoronorvaline (148043-97-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / 10percent aq. NaOH / 1.5 h / Heating

2: SOCl₂ / 0.5 h / Heating

3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, from -78 deg C to RT, 3 h

4: 1.) (i-Pr)2NEt, Bu₂BOTf, 2.) NBS / 1.) CH₂Cl₂, from -78 deg C to 0 deg C, 75 min, 2.) CH₂Cl₂, -78 deg C, 1.25 h

5: 76 percent / tetramethylguanidinium azide / CH₂Cl₂ / 3 h / 0 °C

6: 82 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 0.5 h / 0 °C

7: 81 percent / H₂, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr

With lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; thionyl chloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; acetic acid; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(S)-2-azido-4,4-difluoropentanoic acid

(4S)-4-(2,2-difluoropropyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one

(4S)-4-(3-bromo-2-oxopropyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one

(S)-2,2-Bis(trifluormethyl)-4-(3-diazo-2-oxopropyl)-1,3-oxazolidin-5-on