(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

Base Information

Chemical Name:(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate
CAS No.:154129-94-9
Molecular Formula:C₂₆H₃₀N₂O₄S
Molecular Weight:466.601
Hs Code.:

Synonyms:(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

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Chemical Property of (S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

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Technology Process of (S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

There total 9 articles about (S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate 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: 97.0%

: 108-24-7
acetic anhydride

: 154129-83-6
(1'S,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole

: 154129-94-9
(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

Guidance literature:: With pyridine; dmap; for 6h; Ambient temperature;
DOI:10.1055/s-1993-26021

Reference yield:

: 66399-75-5,84028-90-0
(S)-2-benzylamino-3-phenyl-propionic acid methyl ester

: 154129-94-9
(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

Guidance literature:: Multi-step reaction with 6 steps

1: NaBH₄ / dioxane / 18 h / Ambient temperature

2: 91 percent / BuLi / hexane; diethyl ether / 4 h / -65 °C

3: 95 percent / TFA / H₂O / 0.5 h / Ambient temperature

4: 92 percent / DIBAH / tetrahydrofuran; toluene / 1.) -78 deg C, 1 h; 2.) rt., 30 min

5: dioxane / 18 h / Ambient temperature

6: 97 percent / pyridine / DMAP / 6 h / Ambient temperature

With pyridine; sodium tetrahydroborate; n-butyllithium; diisobutylaluminium hydride; trifluoroacetic acid; dmap; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; water; toluene;
DOI:10.1055/s-1993-26021

Reference yield:

: 68870-85-9,120408-13-1,137693-23-3,40216-77-1
(S)-2-(benzylidene-amino)-3-phenyl-propionic acid methyl ester

: 154129-94-9
(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄ / methanol / 0.5 h / 0 °C

2: NaBH₄ / dioxane / 18 h / Ambient temperature

3: 91 percent / BuLi / hexane; diethyl ether / 4 h / -65 °C

4: 95 percent / TFA / H₂O / 0.5 h / Ambient temperature

5: 92 percent / DIBAH / tetrahydrofuran; toluene / 1.) -78 deg C, 1 h; 2.) rt., 30 min

6: dioxane / 18 h / Ambient temperature

7: 97 percent / pyridine / DMAP / 6 h / Ambient temperature

With pyridine; sodium tetrahydroborate; n-butyllithium; diisobutylaluminium hydride; trifluoroacetic acid; dmap; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; water; toluene;
DOI:10.1055/s-1993-26021