(E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester
CAS No.:1026975-73-4
Molecular Formula:C₃₅H₄₆FN₃O₈
Molecular Weight:655.764
Hs Code.:

(E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

Synonyms:(E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

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Chemical Property of (E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

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Technology Process of (E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

There total 11 articles about (E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl 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:

: 41153-30-4,57292-45-2,79561-25-4,129101-25-3
Boc-Phe(p-F)

: (E)-(S)-4-Amino-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester; hydrochloride

: 1026975-73-4
(E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 23 ℃; for 1.5h;
DOI:10.1021/jm9805384

Reference yield:

: 136904-77-3
(4S)-4-(2-methoxycarbonylethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 1026975-73-4
(E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: aq. 4.0 M NaOH / methanol / 3.5 h / 23 °C

2: 1.) pivaloyl chloride, Et₃N, 2.) LiCl / 1.) THF, 0 deg C, 3.5 h, 2.) THF, 23 deg C, 19 h

3: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 3 h, b) -45 deg C, 2 h

4: 1.) BH₃*THF, 2.) aq. NaBO₃*4H₂O / 1.) THF, 0 deg C, 30 min, 2.) THF, 25 deg C, 1 h

5: 3.53 g / SO₃*pyridine, Et₃N / dimethylsulfoxide / 3 h / 23 °C

6: NaOAc, NaBH₃CN / tetrahydrofuran; ethanol / 20 h / 23 °C

7: p-TsOH*H₂O / methanol / 2.5 h / 50 °C

8: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 1.5 h

9: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 45 min

10: 4.0 M HCl / dioxane / 1.5 h / 23 °C

11: N,N-diisopropylethylamine, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dimethylformamide / 1.5 h / 23 °C

With hydrogenchloride; sodium perborate; sodium hydroxide; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm9805384

Reference yield:

: 223526-25-8
(4S)-4-(2'-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 1026975-73-4
(E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) pivaloyl chloride, Et₃N, 2.) LiCl / 1.) THF, 0 deg C, 3.5 h, 2.) THF, 23 deg C, 19 h

2: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 3 h, b) -45 deg C, 2 h

3: 1.) BH₃*THF, 2.) aq. NaBO₃*4H₂O / 1.) THF, 0 deg C, 30 min, 2.) THF, 25 deg C, 1 h

4: 3.53 g / SO₃*pyridine, Et₃N / dimethylsulfoxide / 3 h / 23 °C

5: NaOAc, NaBH₃CN / tetrahydrofuran; ethanol / 20 h / 23 °C

6: p-TsOH*H₂O / methanol / 2.5 h / 50 °C

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 1.5 h

8: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 45 min

9: 4.0 M HCl / dioxane / 1.5 h / 23 °C

10: N,N-diisopropylethylamine, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dimethylformamide / 1.5 h / 23 °C

With hydrogenchloride; sodium perborate; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm9805384