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Cas Database

1262660-94-5

1262660-94-5

Identification

  • Product Name:C21H28N2O5S

  • CAS Number: 1262660-94-5

  • EINECS:

  • Molecular Weight:420.53

  • Molecular Formula: C21H28N2O5S

  • HS Code:

  • Mol File:1262660-94-5.mol

Synonyms:C21H28N2O5S

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Relevant articles and documentsAll total 2 Articles be found

Synthesis and peptide coupling of protected 2-pyrrolylalanine

D?rr, Aurélie A.,Lubell, William D.

, p. 2159 - 2161 (2011)

2-Pyrrolylalanine has been synthesized in two protected forms and applied in the solution-phase synthesis of a dipeptide. (2S)-N-(Boc)-N′- (phenylsulfonyl)- and (2S)-N,N′-bis-(phenylsulfonyl)-3-(2-pyrrolyl) alanines (7 and 9) were obtained, respectively, in 14% and 13% overall yields and six and seven steps from oxazolidine β-methyl ester 1, which was derived from l-aspartic acid. Homoallylic ketone 2 was obtained from a copper-catalyzed cascade addition of vinylmagnesium bromide to 1 and converted into pyrrolylalanines 7 and 9 by a sequence featuring subsequent olefin oxidation and Paal-Knorr condensation. Protected pyrrolylalanine 9 was then introduced into a dipeptide. Crown Copyright

Synthesis of protected 2-pyrrolylalanine for peptide chemistry and examination of its influence on prolyl amide isomer equilibrium

Doerr, Aurelie A.,Lubell, William D.

, p. 6414 - 6422 (2012/10/08)

Protected enantiopure 2-pyrrolylalanine was synthesized for application in peptide science as an electron-rich arylalanine (histidine) analog with π-donor capability. (2S)-N-(Boc)-N′-(Phenylsulfonyl)-, (2S)-N,N′-bis-(phenylsulfonyl)-, and (2S)-N,N′-bis-(Boc)-3-(2- pyrrolyl)alanines (10, 3, and 14, respectively) were made in 13-17% overall yields and six to seven steps from oxazolidine β-methyl ester 4. Homoallylic ketone 5 was prepared by a copper-catalyzed cascade addition of vinylmagnesium bromide to ester 4 and converted to pyrrolyl amino alcohol 7 by olefin oxidation and Paal-Knorr condensation. Protecting group shuffle and oxidation of the primary alcohol enabled the synthesis of pyrrolylalanines. The bis-Boc analog 14 proved useful in peptide chemistry and was employed to make N-acetyl-pyrrolylalaninyl-proline N′′-methylamide 25. A study of the influence of the pyrrole moiety on the prolyl amide isomer equilibrium of 25 using 1H NMR spectroscopy in chloroform, DMSO, and water demonstrated that the pyrrolylalanine peptide exhibited behavior and conformations different from those of other arylalanine analogs.

Process route upstream and downstream products

Process route

C<sub>15</sub>H<sub>24</sub>N<sub>2</sub>O<sub>3</sub>
1262660-93-4

C15H24N2O3

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

Conditions
Conditions Yield
With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; at 0 ℃;
80%
With 18-crown-6 ether; potassium tert-butylate; In tetrahydrofuran; at 0 ℃; Inert atmosphere;
80%
C<sub>16</sub>H<sub>27</sub>NO<sub>4</sub>
940312-40-3

C16H27NO4

C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water
2: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C
3: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C
With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium tert-butylate; ammonium formate; sodium acetate; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 2: Paal-Knorr condensation;
Multi-step reaction with 3 steps
1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / Inert atmosphere
2: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C / Inert atmosphere
3: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere
With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium tert-butylate; ammonium formate; sodium acetate; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 2: Paal-Knorr condensation;
methyl [(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]ethanoate
205491-14-1

methyl [(4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]ethanoate

C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: copper(l) cyanide / tetrahydrofuran / -45 °C
2: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water
3: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C
4: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C
With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium tert-butylate; ammonium formate; sodium acetate; copper(l) cyanide; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 3: Paal-Knorr condensation;
Multi-step reaction with 4 steps
1: copper(l) cyanide / tetrahydrofuran / -45 °C / Inert atmosphere
2: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / Inert atmosphere
3: ammonium formate; sodium acetate; acetic acid / acetonitrile / 65 °C / Inert atmosphere
4: 18-crown-6 ether; potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere
With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium tert-butylate; ammonium formate; sodium acetate; copper(l) cyanide; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; 3: Paal-Knorr condensation;
C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

C<sub>18</sub>H<sub>24</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-95-6

C18H24N2O5S

Conditions
Conditions Yield
With water; acetic acid; at 50 ℃;
81%
With acetic acid; In water; at 50 ℃; Inert atmosphere;
81%
C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

C<sub>13</sub>H<sub>16</sub>N<sub>2</sub>O<sub>3</sub>S

C13H16N2O3S

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: water; acetic acid / 50 °C
2: trifluoroacetic acid / dichloromethane
With water; acetic acid; trifluoroacetic acid; In dichloromethane;
Multi-step reaction with 2 steps
1.1: acetic acid / water / 50 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / Inert atmosphere
2.2: Inert atmosphere
With acetic acid; trifluoroacetic acid; In dichloromethane; water;
C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

(2S)-N,N'-bis-(phenylsulfonyl)-3-(2-pyrrolyl)alaninol
1262660-96-7

(2S)-N,N'-bis-(phenylsulfonyl)-3-(2-pyrrolyl)alaninol

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: water; acetic acid / 50 °C
2: trifluoroacetic acid / dichloromethane
3: sodium carbonate / 1,4-dioxane; water
With water; sodium carbonate; acetic acid; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water;
Multi-step reaction with 3 steps
1.1: acetic acid / water / 50 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / Inert atmosphere
2.2: Inert atmosphere
3.1: sodium carbonate / 1,4-dioxane; water / Inert atmosphere
With sodium carbonate; acetic acid; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water;
C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

(2S)-N,N'-bis-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1262660-97-8

(2S)-N,N'-bis-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: water; acetic acid / 50 °C
2: trifluoroacetic acid / dichloromethane
3: sodium carbonate / 1,4-dioxane; water
4: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; sodium carbonate; acetic acid; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; acetonitrile;
Multi-step reaction with 4 steps
1.1: acetic acid / water / 50 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / Inert atmosphere
2.2: Inert atmosphere
3.1: sodium carbonate / 1,4-dioxane; water / Inert atmosphere
4.1: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / Inert atmosphere; aq. phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium carbonate; acetic acid; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; acetonitrile;
C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine
1294518-17-4

(2S)-N-(Boc)-N'-(phenylsulfonyl)-3-(2-pyrrolyl)alanine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: water; acetic acid / 50 °C
2: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; acetic acid; In acetonitrile;
Multi-step reaction with 2 steps
1: acetic acid / water / 50 °C / Inert atmosphere
2: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / Inert atmosphere; aq. phosphate buffer
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid; In water; acetonitrile;
C<sub>21</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>S
1262660-94-5

C21H28N2O5S

N,N'-bis-(phenylsulfonyl)-3-(2-pyrrolyl)alaninyl-proline N'-methylamide
1262660-98-9

N,N'-bis-(phenylsulfonyl)-3-(2-pyrrolyl)alaninyl-proline N'-methylamide

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: water; acetic acid / 50 °C
2: trifluoroacetic acid / dichloromethane
3: sodium carbonate / 1,4-dioxane; water
4: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium-phosphate buffer
5: benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / acetonitrile / 0 °C
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; sodium carbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; acetonitrile;

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