N-CBZ-cis-4-hydroxy-L-proline ethyl ester

Base Information

Chemical Name:N-CBZ-cis-4-hydroxy-L-proline ethyl ester
CAS No.:130930-26-6
Molecular Formula:C₁₅H₁₉NO₅
Molecular Weight:293.32
Hs Code.:
DSSTox Substance ID:DTXSID001125639

Synonyms:N-CBZ-cis-4-hydroxy-L-proline ethyl ester;SCHEMBL8477557;FEPRPINUVNZMRY-STQMWFEESA-N;DTXSID001125639;130930-26-6;N-(benzyloxycarbonyl)-cis-4-hydroxy-L-proline ethyl ester;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 2-ethyl 1-(phenylmethyl) ester, (2S-cis)-

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Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-CBZ-cis-4-hydroxy-L-proline ethyl ester

Chemical Property:

XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:293.12632271
Heavy Atom Count:21
Complexity:367

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCOC(=O)C1CC(CN1C(=O)OCC2=CC=CC=C2)O
Isomeric SMILES:CCOC(=O)[C@@H]1C[C@@H](CN1C(=O)OCC2=CC=CC=C2)O

Technology Process of N-CBZ-cis-4-hydroxy-L-proline ethyl ester

There total 5 articles about N-CBZ-cis-4-hydroxy-L-proline ethyl 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: 83.0%

: 64-17-5
ethanol

: 13504-86-4
(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline

: 130930-26-6
N-(benzyloxycarbonyl)-cis-4-hydroxy-L-proline ethyl ester

Guidance literature:: With toluene-4-sulfonic acid; for 36h; Heating;
DOI:10.1021/jm00106a037

Reference yield:

: 64187-47-9
1-benzyloxycarbonyl-4-keto-L-proline

: 130930-26-6
N-(benzyloxycarbonyl)-cis-4-hydroxy-L-proline ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaBH₄ / methanol; H₂O / 20 h / -5 °C

2: 83 percent / p-toluenesulfonic acid / 36 h / Heating

With sodium tetrahydroborate; toluene-4-sulfonic acid; In methanol; water;
DOI:10.1021/jm00106a037

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 130930-26-6
N-(benzyloxycarbonyl)-cis-4-hydroxy-L-proline ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / NaHCO₃ / H₂O; toluene / 16 h / Ambient temperature

2: Jones reagent / acetone / 2.25 h / Ambient temperature

3: NaBH₄ / methanol; H₂O / 20 h / -5 °C

4: 83 percent / p-toluenesulfonic acid / 36 h / Heating

With sodium tetrahydroborate; jones reagent; sodium hydrogencarbonate; toluene-4-sulfonic acid; In methanol; water; acetone; toluene;
DOI:10.1021/jm00106a037