5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

Base Information

Chemical Name:5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester
CAS No.:186521-38-0
Molecular Formula:C₁₆H₂₅NO₅S
Molecular Weight:343.444
Hs Code.:
DSSTox Substance ID:DTXSID50443882
Wikidata:Q76415924
Mol file:186521-38-0.mol

Synonyms:186521-38-0;5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester;Ethyl 5-[(3R)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]thiophene-2-carboxylate;SCHEMBL6989772;DTXSID50443882;GWEQEUZMSNICKD-LLVKDONJSA-N

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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 5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

Chemical Property:

PSA：116.59000
LogP:2.94740
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:10
Exact Mass:343.14534407
Heavy Atom Count:23
Complexity:396

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCOC(=O)C1=CC=C(S1)CCC(CNC(=O)OC(C)(C)C)O
Isomeric SMILES:CCOC(=O)C1=CC=C(S1)CC[C@H](CNC(=O)OC(C)(C)C)O

Technology Process of 5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

There total 6 articles about 5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid 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:

: 24424-99-5
di-tert-butyl dicarbonate

: 186521-37-9
5-(4-Azido-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

: 186521-38-0
5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 2h; under 1551.4 - 2327.2 Torr;
DOI:10.1021/jm9607459

Reference yield:

: 5751-83-7
ethyl 5-bromothiophene-2-carboxylate

: 186521-38-0
5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: CuI, (Ph₃P)2PdCl₂ / diethylamine / Ambient temperature

2: H₂ / 5percent Pd-C / ethanol / 3.5 h / 2327.2 Torr

3: 98 percent / p-toluenesulfonic acid monohydrate, EtOH / 3 h / 65 °C

4: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) RT, 18 h

5: 94 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: 64 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature

7: 82 percent / NaH / tetrahydrofuran / 120 h

8: 79 percent / Mg(ClO₄)2, NaN₃ / acetonitrile / 36 h / 75 °C

9: H₂ / 5percent Pd-C / tetrahydrofuran / 2 h / 1551.4 - 2327.2 Torr

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium azide; magnesium(II) perchlorate; ethanol; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; diethylamine; acetonitrile;
DOI:10.1021/jm9607459

Reference yield:

: 186521-22-2,208337-83-1
5-(3(S)-4-dihydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

: 186521-38-0
5-(4-tert-Butoxycarbonylamino-3(R)-hydroxy-butyl)-thiophene-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) RT, 18 h

2: 94 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 64 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature

4: 82 percent / NaH / tetrahydrofuran / 120 h

5: 79 percent / Mg(ClO₄)2, NaN₃ / acetonitrile / 36 h / 75 °C

6: H₂ / 5percent Pd-C / tetrahydrofuran / 2 h / 1551.4 - 2327.2 Torr

With dmap; sodium azide; magnesium(II) perchlorate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jm9607459