(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate

Base Information

Chemical Name:(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate
CAS No.:154129-95-0
Molecular Formula:C₂₃H₃₂N₂O₄S
Molecular Weight:432.584
Hs Code.:

Synonyms:(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate

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Chemical Property of (S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate

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Technology Process of (S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate

There total 8 articles about (S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl 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: 92.0%

: 108-24-7
acetic anhydride

: 154129-84-7
(1,s,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-4-methylpentyl>-1,3-thiazole

: 154129-95-0
(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate

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

Reference yield:

: 2666-93-5
(S)-Leu-OMe

: 154129-95-0
(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

2: NaBH₄ / methanol / 0.5 h / 0 °C

3: NaBH₄ / dioxane / 18 h / Ambient temperature

4: 93 percent / BuLi / hexane; diethyl ether / 4 h / -65 °C

5: 93 percent / TFA / H₂O / 0.5 h / Ambient temperature

6: 1.) anhydrous zinc chloride; 2.) DIBAH / tetrahydrofuran; toluene / 1.) rt., 1 h ; 2.) -78 deg C, 1 h

7: dioxane / 18 h / Ambient temperature

8: 92 percent / pyridine / DMAP / 6 h / Ambient temperature

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

Reference yield:

: 75691-28-0
methyl (S)-2-(benzylideneamino)-4-methylpentanoate

: 154129-95-0
(S,S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl 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: 93 percent / BuLi / hexane; diethyl ether / 4 h / -65 °C

4: 93 percent / TFA / H₂O / 0.5 h / Ambient temperature

5: 1.) anhydrous zinc chloride; 2.) DIBAH / tetrahydrofuran; toluene / 1.) rt., 1 h ; 2.) -78 deg C, 1 h

6: dioxane / 18 h / Ambient temperature

7: 92 percent / pyridine / DMAP / 6 h / Ambient temperature

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