(2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid

Base Information

Chemical Name:(2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid
CAS No.:360558-40-3
Molecular Formula:C₂₃H₂₄FNO₄
Molecular Weight:397.446
Hs Code.:

Synonyms:(2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid

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Chemical Property of (2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid

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Technology Process of (2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid

There total 1 articles about (2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid 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: 70.0%

: 141018-37-3
(3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole

: 360558-35-6
(S)-fluoroiodoacetic acid

: 360558-40-3
(2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid

Guidance literature:: (3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole; With n-butyllithium; lithium chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(S)-fluoroiodoacetic acid; In tetrahydrofuran; hexane; at -60 ℃; for 17h; Further stages.;
DOI:10.1021/ja010113y

Reference yield: 91.0%

: 360558-40-3
(2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 360558-41-4
(2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid methyl ester

Guidance literature:: In methanol; hexane; benzene; at 23 ℃; for 0.5h;
DOI:10.1021/ja010113y

Reference yield:

: 360558-40-3
(2R,3S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-fluoro-4-oxo-butyric acid

: (S)-1-[(2R,3R,4S)-3-Fluoro-2-hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / benzene; methanol; hexane / 0.5 h / 23 °C

2: 89 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 23 °C

3: NaBH₄ / ethanol / 25 h / -70 - 0 °C

4: 818 mg / t-BuOK / tetrahydrofuran / 0.75 h / 0 °C

5: propan-2-ol / 11 h / Heating

6: 198.0 mg / aq. HCl / 0 - 23 °C

7: 84 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 4 h / 23 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; sodium tris(acetoxy)borohydride; In tetrahydrofuran; methanol; ethanol; hexane; 1,2-dichloro-ethane; isopropyl alcohol; benzene;
DOI:10.1021/ja010113y