(S)-tert-butyl 2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate
• CAS No.: 160800-65-7
• Molecular Formula: C23H36N2O5
• Molecular Weight: 420.549
• Mol file: 160800-65-7.mol

Synonyms:

Chemical Property of (S)-tert-butyl 2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

Chemical Property:

• Melting Point: 55-57 °C
• Boiling Point: 589.1±50.0 °C(Predicted)
• PKA: 13.66±0.20(Predicted)
• PSA: 88.10000
• Density: 1.125±0.06 g/cm3(Predicted)
• LogP: 3.60410

Purity/Quality:

99%, ^*data from raw suppliers

Boc-Dap-NE ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate

There total 9 articles about (S)-tert-butyl 2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidine-1-carboxylate 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: 98.0%

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) + N-Boc-(2R,3R,4S)-dolaproine (120205-50-7) → tert-butyl (2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate (160800-65-7)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 6h; Inert atmosphere;

Reference yield: 88.0%

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) + (2R,3R)-3-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropionic acid dicyclohexylamine salt (1369427-40-6) → tert-butyl (2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate (160800-65-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; diethyl dicarbonate; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/acs.jnatprod.7b00359

Reference yield:

(2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-hydroxy-2-methylpropanoic acid (133565-38-5) → tert-butyl (2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate (160800-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran; mineral oil / 72 h / 0 °C / Inert atmosphere

2: triethylamine; diethyl cyanophosphonate / N,N-dimethyl-formamide / 6 h / 0 - 20 °C / Inert atmosphere

With diethyl cyanophosphonate; sodium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

(1S,2R)-(+)-norphedrine

N-Boc-(2R,3R,4S)-dolaproine

Boc-L-Pro-H

(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine

Downstream raw materials:

(2R,3R)-N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]-3-methoxy-2-methyl-3-[(2S)-pyrrolidin-2-yl]propanamide, trifluoroacetic acid salt

[3H]-Vedotin

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

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