149606-27-9

Basic information

• Product Name: (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide
• Synonyms: (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide;TZT 1027;Soblidotin;Auristatin PE;TZT-1027(Soblidotin)
• CAS NO: 149606-27-9
• Molecular Formula: C₃₉H₆₇N₅O₆
• Molecular Weight: 701.98
• Mol File: 149606-27-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 73-79 °C
• Boiling Point: 843.4°Cat760mmHg
• Flash Point: 463.9°C
• Appearance: /
• Density: 1.064g/cm³
• Vapor Pressure: 1.1E-28mmHg at 25°C
• Refractive Index: 1.514
• PKA: 13.95±0.46(Predicted)
• CAS DataBase Reference: (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide(149606-27-9)
• EPA Substance Registry System: (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide(149606-27-9)

Safety Data

• Hazardous Substances Data: 149606-27-9(Hazardous Substances Data)

Usage

General Description

The chemical compound (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3-methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyrrolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide is a complex organic molecule with multiple functional groups. It contains amino, carboxylic acid, and amide groups, as well as a variety of aromatic and aliphatic hydrocarbon chains. The compound likely exhibits a range of biochemical and pharmacological activities due to its structural complexity and the presence of multiple chiral centers. The detailed structure suggests potential interactions with biological targets and possible therapeutic or diagnostic applications.

InChI:InChI=1/C39H67N5O6/c1-13-27(6)35(43(10)39(48)33(25(2)3)41-38(47)34(26(4)5)42(8)9)31(49-11)24-32(45)44-23-17-20-30(44)36(50-12)28(7)37(46)40-22-21-29-18-15-14-16-19-29/h14-16,18-19,25-28,30-31,33-36H,13,17,20-24H2,1-12H3,(H,40,46)(H,41,47)/t27-,28+,30-,31+,33-,34-,35+,36+/m0/s1

Synthetic route

phenethylamine (64-04-0) + Dov-Val-Dil-Dap (163768-53-4) → TZT-1027 (149606-27-9)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide Yield given;
With triethylamine; diethyl cyano phosphate In DMF (N,N-dimethyl-formamide)

(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid (135383-56-1) → TZT-1027 (149606-27-9)

Conditions

Yield

Multi-step reaction with 9 steps 1: H2SO4 / CH2Cl2 2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 3: 1,3-dicyclohexylcarbodiimide / CH2Cl2 4: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 5: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 6: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature 7: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 8: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 9: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate (120205-58-5) → TZT-1027 (149606-27-9)

Conditions

Yield

Multi-step reaction with 8 steps 1: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 2: 1,3-dicyclohexylcarbodiimide / CH2Cl2 3: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 4: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 5: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature 6: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 7: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 8: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate (474645-22-2) → TZT-1027 (149606-27-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: 1,3-dicyclohexylcarbodiimide / CH2Cl2 2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 3: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 4: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature 5: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 6: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 7: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

(3R,4S,5S)-tert-butyl 4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate (120205-53-0) → TZT-1027 (149606-27-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature 2: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 3: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 4: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate (120205-52-9) → TZT-1027 (149606-27-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 2: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 3: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature 4: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 5: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 6: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

Dov-Val-Dil-Dap-OBzl (163768-52-3) → TZT-1027 (149606-27-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 2: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

(3R,4S,5S)-4-[(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate (177423-00-6) → TZT-1027 (149606-27-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 2: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature 3: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 4: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 5: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

(3R,4S,5S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxy-5-methyl-heptanoic acid methyl ester (149664-79-9) → TZT-1027 (149606-27-9)

Conditions

Yield

Multi-step reaction with 10 steps 1: 1N aq. NaOH / dioxane / 3 h / Ambient temperature 2: H2SO4 / CH2Cl2 3: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 4: 1,3-dicyclohexylcarbodiimide / CH2Cl2 5: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 6: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 7: trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature 8: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 9: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 10: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

(3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoic acid (133120-89-5) → TZT-1027 (149606-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl phosphorocyanidate, Et3N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h 2: H2 / 5percent Pd/C / 2-methyl-propan-2-ol; H2O / 2 h 3: diethyl phosphorocyanidate, Et3N / dimethylformamide View Scheme

3-methoxy-2-methyl-N-phenethyl-3-pyrrolidin-2-yl-propionamide + (3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoic acid (133120-89-5) → TZT-1027 (149606-27-9)

Conditions	Yield
With triethylamine; diethyl cyano phosphate In DMF (N,N-dimethyl-formamide)

Upstream product

• 120205-53-0 (3R,4S,5S)-tert-butyl 4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate 
• 120205-52-9 tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 
• 133120-89-5 (3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoic acid 
• 149664-79-9 (3R,4S,5S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxy-5-methyl-heptanoic acid methyl ester 
• 177423-00-6 (3R,4S,5S)-4-[(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 
• 163768-52-3 Dov-Val-Dil-Dap-OBzl 
• 474645-22-2 tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate 
• 120205-58-5 tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate 
• 135383-56-1 (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid 
• 64-04-0 phenethylamine 
• 163768-53-4 Dov-Val-Dil-Dap 

Relevant articles and documents

TETRAPEPTIDE DERIVATIVE CRYSTALS

The invention provides crystals of N2-(N,N-dimethyl-L-valyl)-N-[(1S,2R)-2-methoxy-4-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[(2-phenylethyl)amino]propyl]-2-pyrrolidinyl]-1-[(S)-1-methylpropyl ]- 4-oxobutyl]-N-methyl-L-valinamide or salts thereof which possess potent antitumor activity and methods for their preparation.