(S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester

Base Information

Chemical Name:(S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester
CAS No.:952193-68-9
Molecular Formula:C₂₂H₃₀N₂O₅
Molecular Weight:402.491
Hs Code.:

Synonyms:(S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester

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Chemical Property of (S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester

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Technology Process of (S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester

There total 6 articles about (S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl 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: 90.0%

: 952193-65-6
(S)-1-(tert-butoxycarbonylamino)-3-cyclohexene-1-carboxylic acid

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: 952193-68-9
(S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60 ℃; for 0.5h; microwave irradiation;
DOI:10.1016/j.tet.2007.06.108

Reference yield:

: 241161-71-7
(2R,5S)-5-(3-butenyl)-3,6-diethoxy-2,5-dihydro-2-isopropylpyrazine

: 952193-68-9
(S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 80 percent / tetrahydrofuran; hexane / 16 h / -78 - 20 °C

2.1: 85 percent / Grubbs second generation catalyst / CH₂Cl₂ / 0.25 h / 140 °C / microwave irradiation

3.1: TFA; water / acetonitrile / 0.33 h / 60 °C / microwave irradiation

4.1: 0.50 g / tetrahydrofuran / 20 h / Heating

5.1: 93 percent / lithium hydroxide / tetrahydrofuran; H₂O / 0.33 h / 60 °C / microwave irradiation

6.1: 90 percent / HATU; DIPEA / dimethylformamide / 0.5 h / 60 °C / microwave irradiation

With lithium hydroxide; n-butyllithium; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2007.06.108

Reference yield:

: 952193-56-5
(2R,5S)-5-allyl-5-(3-butenyl)-3,6-diethoxy-2,5-dihydro-2-isopropylpyrazine

: 952193-68-9
(S)-N-[(1-(tert-butoxycarbonylamino)-cyclohex-3-enyl)carbonyl]-L-phenylalanine methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / Grubbs second generation catalyst / CH₂Cl₂ / 0.25 h / 140 °C / microwave irradiation

2: TFA; water / acetonitrile / 0.33 h / 60 °C / microwave irradiation

3: 0.50 g / tetrahydrofuran / 20 h / Heating

4: 93 percent / lithium hydroxide / tetrahydrofuran; H₂O / 0.33 h / 60 °C / microwave irradiation

5: 90 percent / HATU; DIPEA / dimethylformamide / 0.5 h / 60 °C / microwave irradiation

With lithium hydroxide; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2007.06.108