(S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

Base Information

Chemical Name:(S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester
CAS No.:685545-27-1
Molecular Formula:C₂₇H₃₉N₅O₆
Molecular Weight:529.637
Hs Code.:

Synonyms:(S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

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Chemical Property of (S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

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Technology Process of (S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

There total 16 articles about (S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic 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:

: 34702-66-4
8-benzyl-2-oxa-8-aza-spiro[4.5]decane-1,3-dione

: 685545-27-1
(S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Et₃N / dimethylformamide / 20 °C

2.1: 3.40 g / acetic anhydride; NaOAc / 2 h / Heating

3.1: NaBH₄ / methanol / 0 - 20 °C

3.2: NaBH₄; TFA / 0 - 20 °C

3.3: 792 mg / acetonitrile; CH₂Cl₂ / 20 °C

4.1: 74 percent / aq. NH₄OAc; Cd-Pb couple / tetrahydrofuran / 20 °C

5.1: 85 percent / HBTU; DIEA / dimethylformamide / 17 h / 20 °C

6.1: hydroxylamine hydrochloride; Et₃N / ethanol / 50 °C

7.1: acetic acid / 20 °C

8.1: H₂; acetic acid / Pd/C / 760 Torr

With sodium tetrahydroborate; 10% Cd/Pd; hydroxylamine hydrochloride; ammonium acetate; hydrogen; sodium acetate; acetic anhydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jm030354b

Reference yield:

: 3612-20-2
1-phenylmethyl-4-piperidone

: 685545-27-1
(S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: Et₃N; molecular sieves 4A / CH₂Cl₂ / 20 °C

2.1: 55.10 g / ethanol; H₂O / 2 h / Heating

3.1: 98 percent / aq. HCl / 72 h / Heating

4.1: DCC / dimethylformamide / 2 h / 20 °C

5.1: Et₃N / dimethylformamide / 20 °C

6.1: 3.40 g / acetic anhydride; NaOAc / 2 h / Heating

7.1: NaBH₄ / methanol / 0 - 20 °C

7.2: NaBH₄; TFA / 0 - 20 °C

7.3: 792 mg / acetonitrile; CH₂Cl₂ / 20 °C

8.1: 74 percent / aq. NH₄OAc; Cd-Pb couple / tetrahydrofuran / 20 °C

9.1: 85 percent / HBTU; DIEA / dimethylformamide / 17 h / 20 °C

10.1: hydroxylamine hydrochloride; Et₃N / ethanol / 50 °C

11.1: acetic acid / 20 °C

12.1: H₂; acetic acid / Pd/C / 760 Torr

With hydrogenchloride; sodium tetrahydroborate; 10% Cd/Pd; 4 A molecular sieve; hydroxylamine hydrochloride; ammonium acetate; hydrogen; sodium acetate; acetic anhydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Knoevenagel condensation;
DOI:10.1021/jm030354b

Reference yield:

: 3886-08-6
5-tert-butyl N-benzyloxycarbonyl-L-glutamate

: 685545-27-1
(S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 83 percent / EDC*HCl; HOBt / dimethylformamide / 16 h / 20 °C

2: 91 percent / H₂ / Pd(OH)2/C / ethanol / 7 h / 2585.74 Torr

3: 86 percent / DIEA / CH₂Cl₂ / 20 h / 20 °C

4: 96 percent / TFA / 5 h / 20 °C

5: 85 percent / HBTU; DIEA / dimethylformamide / 17 h / 20 °C

6: hydroxylamine hydrochloride; Et₃N / ethanol / 50 °C

7: acetic acid / 20 °C

8: H₂; acetic acid / Pd/C / 760 Torr

With hydroxylamine hydrochloride; hydrogen; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm030354b