(S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid

Base Information

Chemical Name:(S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid
CAS No.:1027066-05-2
Molecular Formula:C₂₁H₂₈N₂O₄
Molecular Weight:372.464
Hs Code.:

Synonyms:(S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid

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Chemical Property of (S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid

Chemical Property:

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Technology Process of (S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid

There total 17 articles about (S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid 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:

: 215300-59-7
(2S)-N-[5-benzyloxy-2-[(S)-2-(methoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine benzyl ester

: 1027066-05-2
(S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid

Guidance literature:: With potassium hydroxide; In methanol; water; at 70 ℃;
DOI:10.1016/S0040-4039(98)01598-6

Reference yield:

: 1080-06-4
L-Tyr-OMe

: 1027066-05-2
(S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / NaOH; NaHCO₃ / H₂O; CHCl₃ / 2 h

2: 85 percent / La(NO₃)2*6H₂O; NaNO₃; 6N HCl / CH₂Cl₂ / 6 h / 0 - 20 °C

3: H₂ / Pd/C / ethyl acetate / 22800 Torr

4: 80 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

5: LiBH₄ / tetrahydrofuran / 5 h / 20 °C

6: 78 percent / pyridine / 8 h / 20 °C

7: 61 percent

8: 90 percent / K₂CO₃ / dimethylformamide / 2 h / 50 °C

9: Cu(OAc)2; NaBH₄ / methanol / 0.5 h / 0 °C

10: 64 percent / 2,6-lutidine / 1,2-dichloro-ethane / 72 h / 70 °C

11: 2N KOH / methanol / 24 h / 70 °C

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; sodium tetrahydroborate; lithium borohydride; copper diacetate; lanthanum nitrate; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: NH2-protection / 2: Nitration / 3: Reduction / 4: Acetylation / 5: Reduction / 6: Acetylation / 8: Substitution / 9: Reduction / 10: Substitution / 11: Hydrolysis;
DOI:10.1021/jo990605h

Reference yield:

: 60-18-4,18875-48-4,25619-78-7,30704-25-7
L-tyrosine

: 1027066-05-2
(S)-2-[2-((S)-2-Amino-3-hydroxy-propyl)-5-benzyloxy-phenylamino]-3-methyl-butyric acid

Guidance literature:: Multi-step reaction with 12 steps

1: SOCl₂ / Heating

2: 100 percent / NaOH; NaHCO₃ / H₂O; CHCl₃ / 2 h

3: 85 percent / La(NO₃)2*6H₂O; NaNO₃; 6N HCl / CH₂Cl₂ / 6 h / 0 - 20 °C

4: H₂ / Pd/C / ethyl acetate / 22800 Torr

5: 80 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

6: LiBH₄ / tetrahydrofuran / 5 h / 20 °C

7: 78 percent / pyridine / 8 h / 20 °C

8: 61 percent

9: 90 percent / K₂CO₃ / dimethylformamide / 2 h / 50 °C

10: Cu(OAc)2; NaBH₄ / methanol / 0.5 h / 0 °C

11: 64 percent / 2,6-lutidine / 1,2-dichloro-ethane / 72 h / 70 °C

12: 2N KOH / methanol / 24 h / 70 °C

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; sodium tetrahydroborate; lithium borohydride; thionyl chloride; copper diacetate; lanthanum nitrate; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Esterification / 2: NH2-protection / 3: Nitration / 4: Reduction / 5: Acetylation / 6: Reduction / 7: Acetylation / 9: Substitution / 10: Reduction / 11: Substitution / 12: Hydrolysis;
DOI:10.1021/jo990605h