(2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 693785-89-6
• Molecular Formula: C₃₄H₃₈N₂O₆
• Molecular Weight: 570.686

Synonyms:(2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 7 articles about (2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl 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:

(4R)-1-(tert-butoxycarbonyl)-4-(1-naphthylmethoxy)-L-proline (220424-74-8) + benzyl (1RS,2SR)-1-amino-2-vinylcyclopropanecarboxylate → (2S,4R)-2-((1S,2R)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester + (2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (693785-89-6)

Guidance literature:

With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In acetonitrile; at 20 ℃;

DOI:10.1021/jm030573x

Reference yield:

malonic acid dibenzyl ester (15014-25-2) → (2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (693785-89-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: t-BuOK / tetrahydrofuran / 0.5 h / -30 - -10 °C

1.2: 52 percent / tetrahydrofuran

2.1: aq. LiOH / 2-methyl-propan-2-ol / 72 h / 20 °C

3.1: Et₃N; DPPA / tetrahydrofuran / Heating

3.2: 11.0 g / tetrahydrofuran / Heating

4.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C

5.1: 4.33 g / TBTU; NMM / acetonitrile / 20 °C

With 4-methyl-morpholine; lithium hydroxide; diphenyl-phosphinic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jm030573x

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,4R)-2-((1R,2S)-1-Benzyloxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(naphthalen-1-ylmethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (693785-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 58 percent / tetrahydrofuran / 18 h / Heating

2.1: 4.33 g / TBTU; NMM / acetonitrile / 20 °C

With 4-methyl-morpholine; sodium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm030573x

upstream raw materials:

(4R)-1-(tert-butoxycarbonyl)-4-(1-naphthylmethoxy)-L-proline

malonic acid dibenzyl ester

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

2-(bromomethyl)naphthalene

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