(S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

Base Information

Chemical Name:(S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester
CAS No.:593252-99-4
Molecular Formula:C₃₄H₅₂N₂O₇
Molecular Weight:600.796
Hs Code.:

(S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

Synonyms:(S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

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Chemical Property of (S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

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Technology Process of (S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

There total 19 articles about (S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-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:

: 56564-52-4
N-methyl-D-phenylalanine

: 593252-99-4
(S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 200 mg / HClO₄ / 24 h / cooling

2: 26.7 mg / BEP; DIPEA / CH₂Cl₂ / 14.5 h / -10 - 20 °C

3: H₂; aq. HCl / Pd/C / methanol

4: BEP; DIPEA / CH₂Cl₂ / 14.5 h / -10 - 20 °C

With hydrogenchloride; perchloric acid; hydrogen; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/ol034803d

Reference yield:

: 111-29-5
1 ,5-pentanediol

: 593252-99-4
(S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH

2.1: 71.1 percent / (COCl)2; DMSO / CH₂Cl₂ / 1.17 h / -78 °C

3.1: N-Ts-4-(S)-isopropyl-1,3,2-oxazaborolidinone-5 / tetrahydrofuran; CH₂Cl₂ / 0.17 h / -78 °C

3.2: tetrahydrofuran; CH₂Cl₂ / 2 h

4.1: 2,6-lutidine / CH₂Cl₂ / 2 h / -50 °C

5.1: H₂ / Pd/C / methanol / 20 °C

6.1: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -78 °C

7.1: K₂CO₃ / methanol / 0 - 20 °C

8.1: TFA / CH₂Cl₂ / 0.33 h / 0 °C

9.1: aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C

10.1: BEP; DIPEA / CH₂Cl₂ / 14.5 h / -10 - 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; oxalyl dichloride; hydrogen; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; sodium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 2.1: Swern oxidation / 6.1: Swern oxidation;
DOI:10.1021/ol034803d

Reference yield:

: 72-18-4,25609-85-2,7004-03-7,921-10-8
L-valine

: 593252-99-4
(S)-2-((R)-3-Hydroxy-2,2-dimethyl-oct-7-ynoylamino)-3-methyl-butyric acid (S)-1-[((R)-1-tert-butoxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaNO₂; H₂SO₄ / H₂O

2.1: 86 percent / I₂; PhI(OAc)2 / CH₂Cl₂ / 1.75 h / -10 - 20 °C

3.1: EDCI; DMAP / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 84 percent / CH₂Cl₂ / 0 - 20 °C

4.1: CH₂Cl₂ / 0.17 h / 0 °C

5.1: 26.7 mg / BEP; DIPEA / CH₂Cl₂ / 14.5 h / -10 - 20 °C

6.1: H₂; aq. HCl / Pd/C / methanol

7.1: BEP; DIPEA / CH₂Cl₂ / 14.5 h / -10 - 20 °C

With hydrogenchloride; dmap; [bis(acetoxy)iodo]benzene; sulfuric acid; hydrogen; iodine; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium nitrite; palladium on activated charcoal; In methanol; dichloromethane; water;
DOI:10.1021/ol034803d