N-Boc-cis-4-Hydroxy-L-proline

Base Information

• Chemical Name: N-Boc-cis-4-Hydroxy-L-proline
• CAS No.: 87691-27-8
• Molecular Formula: C10H17NO5
• Molecular Weight: 231.249
• Hs Code.: 29339900
• European Community (EC) Number: 627-315-1
• UNII: H4YCJ0KW0U
• DSSTox Substance ID: DTXSID80350919
• Wikidata: Q27279643
• Mol file: 87691-27-8.mol

Synonyms:87691-27-8;N-Boc-cis-4-Hydroxy-L-proline;(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;cis-1-(tert-Butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;cis-N-Boc-4-hydroxy-L-proline;MFCD02094406;H4YCJ0KW0U;(2S,4S)-1-[(tert-butoxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid;(2S,4S)-cis-1-N-Boc-4-hydroxy-proline;N-Boc-4-hydroxy-L-proline, cis-;(2S,4S)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(S,S)-cis-1-N-Boc-4-hydroxy-proline;N-Boc-4-hydroxy-L-proline, (4S)-(-)-;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) ester, (2S,4S)-;Boc-cis-Hyp-OH;boc-cishyp-oh;(2s,4s)-1-tert-butoxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) ester, (2S-cis)-;N-Boc-cis-4-hydroxypyrrolidine-2-carboxylic acid;(2S,4S)-1-BOC-4-hydroxypyrrolidine-2-carboxylic acid;(4s)-1-(tert-butoxycarbonyl)-4-hydroxy-l-proline;boc-(2s,4s)-(-)-4-hydroxypyrrolidine-2-carboxylic acid;UNII-H4YCJ0KW0U;N-Boc-cis-4-hydroxyproline;SCHEMBL242328;DTXSID80350919;BENKAPCDIOILGV-BQBZGAKWSA-N;BCP09808;N-Boc-(2S,4S)-4-hydroxyproline;AKOS012181862;CS-W002886;HY-W002886;N-Boc-cis-4-hydroxy-L-proline, 97%;AC-24045;AM808177;TS-00616;B5887;BB 0260225;EN300-66086;(4S)-1-t- butoxycarbonyl-4-hydroxy-L-proline;P15624;cis-N-(tert-Butoxycarbonyl)-4-hydroxy-L-proline;(4S)-1-(tert-butoxy carbonyl)-4-hydroxy-L-proline;Q27279643;Z1033300652;(N-Boc-cis-4-Hydroxy-L-proline;(2S, 4S)-1-t-butoxycarbonyl-4-hydroxy-2-pyrrolidinecarboxylic acid;(4s)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-hydroxy-l-proline;(2S,4S)-1-(tert-Butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid;(2S,4S)-1-tert-Butoxycarbonyl-4-hydroxy-pyrrolidine-2-carboxylic acid;(2s,4s)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Chemical Property of N-Boc-cis-4-Hydroxy-L-proline

Chemical Property:

• Vapor Pressure: 9.99E-08mmHg at 25°C
• Melting Point: 146 °C (D)(lit.)
• Refractive Index: 1.531
• Boiling Point: 390.9oC at 760 mmHg
• PKA: 3.80±0.40(Predicted)
• Flash Point: 190.2oC
• PSA: 87.07000
• Density: 1.312 g/cm³
• LogP: 0.37920
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 231.11067264
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

Boc-cis-4-hydroxy-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50
• Safety Statements: 26-36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)O

Technology Process of N-Boc-cis-4-Hydroxy-L-proline

There total 25 articles about N-Boc-cis-4-Hydroxy-L-proline 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: 99.1%

N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8) → N-tert-butoxycarbonyl-L-cis-4-hydroxyproline (87691-27-8,946610-68-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 5 ℃;

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + hydroxy L-proline (618-27-9,30724-02-8) → N-tert-butoxycarbonyl-L-cis-4-hydroxyproline (87691-27-8,946610-68-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; pH=9 - 10;

Reference yield: 92.0%

2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate (87250-97-3,113775-22-7) → N-tert-butoxycarbonyl-L-cis-4-hydroxyproline (87691-27-8,946610-68-0)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.joc.1c00755

upstream raw materials:

N-tert-butoxycarbonyl-4-oxo-L-proline

di-tert-butyl dicarbonate

hydroxy L-proline

(2S,4R)-1-tert-butyl 2-ethyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2S,4S)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-phenyl-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4S)-2-((S)-1-Benzyloxycarbonyl-ethylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

hydroxy L-proline

(2S,4S)-4-Hydroxy-2-((1R,2S)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Zwick, Christian R.,Sosa, Max B.,Renata, Hans. "Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores". supporting information. p. 1673 - 1679. Retrieved 2021/01/25.
• 2、 Ahles, Sebastian,Beeck, Sebastian,Wegner, Hermann A.. "Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels?Alder/Substitution Reaction". supporting information. . Retrieved 2021/12/09.