Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

Base Information

Chemical Name:Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester
CAS No.:158744-42-4
Molecular Formula:C₁₉H₂₄N₂O₄S
Molecular Weight:376.477
Hs Code.:

Synonyms:Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

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Chemical Property of Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

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Technology Process of Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

There total 10 articles about Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl 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: 19.0%

: 219586-42-2
2-<2(S)-(tert-Butoxyformamido)-1-hydroxy-3-phenylpropyl>thiazole

: 108-24-7
acetic anhydride

: 158744-42-4
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

: Acetic acid (1R,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

Guidance literature:: With pyridine; dmap; for 16h; Yields of byproduct given; Ambient temperature;
DOI:10.1021/jo00092a026

Reference yield:

: 169905-25-3
(S,S)-2--3-phenyl-1-(1,3-thiazol-2-yl)propyl acetate

: 158744-42-4
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; for 18h; Yield given; Ambient temperature;
DOI:10.1021/jo00129a057

Reference yield:

: 63-91-2,25191-15-5,658-69-5,67675-33-6
L-phenylalanine

: 158744-42-4
Acetic acid (1S,2S)-2-tert-butoxycarbonylamino-3-phenyl-1-thiazol-2-yl-propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: LAH / tetrahydrofuran / 1 h / Heating

2: molecular sieves 4 Angstroem / toluene / 1 h / 90 °C

3: NaBH₄ / methanol / 30 h / 0 °C

4: 99 percent / dioxane / 18 h / Ambient temperature

5: 1.) (COCl)2, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, - 60 deg C to -45 deg C, 30 min; -45 deg C, 5 min, 2.) 5 min

6: 2.) Bu₄NF*3H₂O / 1.) CH₂Cl₂, -20 deg C, 48 h, 2.) THF, r.t., 1 h

7: 99 percent / pyridine, DMAP / 18 h / Ambient temperature

8: CAN / acetonitrile; H₂O / 18 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water; toluene; acetonitrile;
DOI:10.1021/jo00129a057