2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid

Base Information

Chemical Name:2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid
CAS No.:186132-78-5
Molecular Formula:C₂₀H₂₈N₂O₈S
Molecular Weight:456.517
Hs Code.:

Synonyms:2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid

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Chemical Property of 2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid

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Technology Process of 2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid

There total 10 articles about 2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic 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: 85.0%

: 186132-76-3
2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid 4-nitro-benzyl ester

: 186132-78-5
2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 15h; Ambient temperature;
DOI:10.1002/hlca.19960790816

Reference yield: 61.0%

: 2,2,2-trichloroethyl 2-((4R,7S)-7-(hydroxymethyl)-4-(methoxycarbonyl)-11,11-dimethyl-6,9-dioxo-10-oxa-2-thia-5,8-diazadodecyl)benzoate

: 186132-78-5
2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid

Guidance literature:: With ammonium acetate; zinc; In tetrahydrofuran; water; at 20 ℃; for 2h;
DOI:10.1021/acs.jmedchem.0c01569

Reference yield:

: 40819-28-1
2-(bromomethyl)benzoyl bromide

: 186132-78-5
2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-benzoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 57 percent / (i-Pr)2EtN / CH₂Cl₂ / 0 deg C, 15 min; room temp., 3 h

2: 50 percent / Et₃N / CH₂Cl₂ / 0 deg C, 15 min; room temp., 3 h

3: 63 percent / N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride / acetonitrile / 4 h / 0 °C

4: 85 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h / Ambient temperature

With hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1002/hlca.19960790816