(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Base Information

Chemical Name:(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane
CAS No.:143508-02-5
Molecular Formula:C₃₇H₅₈N₄O₉
Molecular Weight:702.889
Hs Code.:

(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9-<N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

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Chemical Property of (9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

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Technology Process of (9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

There total 15 articles about (9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane 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:

: 1-Amino-6-benzyloxy-hexan-2-ol

: 143508-02-5,143614-63-5
(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Guidance literature:: Multi-step reaction with 13 steps

1: 87 percent / sodium bicarbonate / tetrahydrofuran; H₂O

2: 92 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

3: H₂ / 10 percent Pd/C / methanol / 760 Torr

4: pyridinium dichromate (PDC) / dimethylformamide / 48 h

5: 45 percent / potassium carbonate / acetone / 6 h / Heating

6: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

7: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC), N-methylmorpholine (NMM) / CH₂Cl₂ / 0 - 20 °C

8: H₂ / 10 percent Pd/C / methanol / 760 Torr

9: 4-(dimethylamino)pyridine (DMAP), 4-(dimethylamino)pyridine hydrochloride, 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran; CHCl₃ / 19 h / Heating

10: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

11: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 - 20 °C

12: acetic acid, Zn / 5 h

13: acetic acid, pyridine, sodium cyanoborohydride / H₂O

With 4-methyl-morpholine; pyridine; dmap; dipyridinium dichromate; hydrogen; 4-(dimethylamino)pyridine hydrochloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00099a004

Reference yield:

: 143508-19-4
1-Azido-6-benzyloxy-hexan-2-ol

: 143508-02-5,143614-63-5
(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Guidance literature:: Multi-step reaction with 14 steps

1: H₂ / Raney nickel / methanol

2: 87 percent / sodium bicarbonate / tetrahydrofuran; H₂O

3: 92 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

4: H₂ / 10 percent Pd/C / methanol / 760 Torr

5: pyridinium dichromate (PDC) / dimethylformamide / 48 h

6: 45 percent / potassium carbonate / acetone / 6 h / Heating

7: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

8: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC), N-methylmorpholine (NMM) / CH₂Cl₂ / 0 - 20 °C

9: H₂ / 10 percent Pd/C / methanol / 760 Torr

10: 4-(dimethylamino)pyridine (DMAP), 4-(dimethylamino)pyridine hydrochloride, 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran; CHCl₃ / 19 h / Heating

11: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

12: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 - 20 °C

13: acetic acid, Zn / 5 h

14: acetic acid, pyridine, sodium cyanoborohydride / H₂O

With 4-methyl-morpholine; pyridine; dmap; dipyridinium dichromate; hydrogen; 4-(dimethylamino)pyridine hydrochloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; zinc; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00099a004

Reference yield:

: 143508-20-7
(6-Benzyloxy-2-hydroxy-hexyl)-carbamic acid 2,2,2-trichloro-ethyl ester

: 143508-02-5,143614-63-5
(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Guidance literature:: Multi-step reaction with 12 steps

1: 92 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

2: H₂ / 10 percent Pd/C / methanol / 760 Torr

3: pyridinium dichromate (PDC) / dimethylformamide / 48 h

4: 45 percent / potassium carbonate / acetone / 6 h / Heating

5: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

6: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC), N-methylmorpholine (NMM) / CH₂Cl₂ / 0 - 20 °C

7: H₂ / 10 percent Pd/C / methanol / 760 Torr

8: 4-(dimethylamino)pyridine (DMAP), 4-(dimethylamino)pyridine hydrochloride, 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran; CHCl₃ / 19 h / Heating

9: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

10: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 - 20 °C

11: acetic acid, Zn / 5 h

12: acetic acid, pyridine, sodium cyanoborohydride / H₂O

With 4-methyl-morpholine; pyridine; dmap; dipyridinium dichromate; hydrogen; 4-(dimethylamino)pyridine hydrochloride; sodium cyanoborohydride; potassium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00099a004