2-amino-N-{1-[2H₅]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide

Base Information

• Chemical Name: 2-amino-N-{1-[2H₅]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide
• CAS No.: 856765-80-5
• Molecular Formula: C₂₆H₃₈N₄O₆S
• Molecular Weight: 539.637

Synonyms:2-amino-N-{1-[2H₅]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide

Chemical Property of 2-amino-N-{1-[2H₅]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide

Chemical Property:

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Technology Process of 2-amino-N-{1-[2H₅]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide

There total 7 articles about 2-amino-N-{1-[2H₅]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide 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: 84.0%

N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) + N-(3S-amino-2R-hydroxy-4-[2H5]phenyl-butyl)-N-isobutyl-4-nitro-benzenesulfonamide methanesulfonic acid salt → 2-amino-N-{1-[2H5]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide (856765-80-5)

Guidance literature:

N-tert-butyloxycarbonyl-L-tert-leucine; With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

N-(3S-amino-2R-hydroxy-4-[2H₅]phenyl-butyl)-N-isobutyl-4-nitro-benzenesulfonamide methanesulfonic acid salt; In N,N-dimethyl-formamide;

With methanesulfonic acid; In Isopropyl acetate; at 85 ℃; for 0.5h;

DOI:10.1002/jlcr.870

Reference yield:

S-4-[2H5]benzyl-5S-(benzyloxymethyl)-oxazolidin-2-one (856765-73-6) → 2-amino-N-{1-[2H5]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide (856765-80-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: KOH / ethanol; H₂O / 2 h / 70 °C

1.2: 94 percent / ethanol; H₂O; CH₂Cl₂ / 2 h / 20 °C / pH 7

2.1: 100 percent / hydrogen / Pd/C / ethyl acetate / 18 h

3.1: 1-bromocarbonyl-1-methylethyl acetate / CHCl₃ / 3 h / 20 °C

3.2: 73 percent / NaOMe / tetrahydrofuran / 4 h / 20 °C

4.1: 100 percent / propan-2-ol / 4 h / 86 °C

5.1: 885.8 mg / K₂CO₃ / isopropyl acetate; H₂O / 30 h / 56 °C

6.1: 80 percent / isopropyl acetate / 0.5 h / 85 °C

7.1: 1-hydroxybenzotriazole hydrate; 4-methylmorpholine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide

7.2: dimethylformamide

7.3: 84 percent / methanesulfonic acid / isopropyl acetate / 0.5 h / 85 °C

With 4-methyl-morpholine; potassium hydroxide; acetoxyisobutyryl bromide; hydrogen; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In ethanol; chloroform; Isopropyl acetate; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/jlcr.870

Reference yield:

(S)-1-[N-(tert-butyloxycarbonyl)amino]-1-[2H5]benzyl-3-(benzyloxy)propan-2S-ol (856765-74-7) → 2-amino-N-{1-[2H5]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3,3-dimethylbutyramide (856765-80-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / hydrogen / Pd/C / ethyl acetate / 18 h

2.1: 1-bromocarbonyl-1-methylethyl acetate / CHCl₃ / 3 h / 20 °C

2.2: 73 percent / NaOMe / tetrahydrofuran / 4 h / 20 °C

3.1: 100 percent / propan-2-ol / 4 h / 86 °C

4.1: 885.8 mg / K₂CO₃ / isopropyl acetate; H₂O / 30 h / 56 °C

5.1: 80 percent / isopropyl acetate / 0.5 h / 85 °C

6.1: 1-hydroxybenzotriazole hydrate; 4-methylmorpholine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide

6.2: dimethylformamide

6.3: 84 percent / methanesulfonic acid / isopropyl acetate / 0.5 h / 85 °C

With 4-methyl-morpholine; acetoxyisobutyryl bromide; hydrogen; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In chloroform; Isopropyl acetate; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/jlcr.870

upstream raw materials:

N-tert-butyloxycarbonyl-L-tert-leucine

(1S,2S)-(oxiranyl-2-[2H₅]-phenyl-ethyl)-carbamic acid tert-butyl ester

S-1-[N-(tert-butyloxycarbonyl)amino]-1-[2H₅]benzyl-propan-2S,3-diol

S-4-[2H₅]benzyl-5S-(benzyloxymethyl)-oxazolidin-2-one

Downstream raw materials:

[{1-{1-[2H₅]phenylmethyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propylcarbamoyl}-2,2-dimethyl-propylcarbamoyl}-methyl](3-fluoro-benzyl)-carbamic acid tert-butyl ester

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