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159634-47-6
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Basic Information
CAS No.: 159634-47-6
Name: Ibutamoren
Molecular Structure:
Molecular Structure of 159634-47-6 (Ibutamoren)
Formula: C27H36N4O5S
Molecular Weight: 528.673
Synonyms: L 163191;Propanamide,2-amino-N-[2-[1,2-dihydro-1-(methylsulfonyl)spiro[3H-indole-3,4'-piperidin]-1'-yl]-2-oxo-1-[(phenylmethoxy)methyl]ethyl]-2-methyl-,(R)-;UNII-GJ0EGN38UL;Ibutamoren [INN];1'-(2-Methylalanyl-O-benzyl-D-seryl)-1-(methylsulfonyl)-1,2-dihydrospiro[indole-3,4'-piperidine];Propanamide, 2-amino-N-((1R)-2-(1,2-dihydro-1-(methylsulfonyl)spiro(3H-indole-3,4'-piperidin)-1'-yl)-2-oxo-1-((phenylmethoxy)methyl)ethyl)-2-methyl-;
Density: 1.32 g/cm3
PSA: 130.42000
LogP: 3.94020
Related products
Synthetic route
159634-87-4

N-[(R)-[(1,2-Dihydro-1-methanesulfonylspiro[3H-indole-3,4'-piperidin]-1'-yl)carbonyl]-2-(phenylmethyloxy)ethyl]-2-[(1,1-dimethyl-ethoxy)carbonyl]amino-2-methyl-propanamide

159634-47-6

Ibutamoren

Conditions
ConditionsYield
With methanesulfonic acid In ethanol at 35 - 40℃; Yield given;
498-94-2

isonipecotic acid

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 97 percent / K2CO3 / H2O / 58 h / 22 °C
2: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C
3: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr
4: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
5: NaBH4 / toluene / 0.5 h / -2 °C
6: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
7: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
8: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
9: MsOH / ethanol / 7.5 h / 35 - 40 °C
10: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
11: MsOH / ethanol / 35 - 40 °C
View Scheme
47173-80-8

N-Boc-D-serine(Bzl)-OH

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
2: MsOH / ethanol / 7.5 h / 35 - 40 °C
3: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
4: MsOH / ethanol / 35 - 40 °C
View Scheme
100-39-0

benzyl bromide

potassium-compound of propionic acid-<1-methyl-2-oxo-propylidenehydrazide>

potassium-compound of propionic acid-<1-methyl-2-oxo-propylidenehydrazide>

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 74 percent / NaOt-Am / dimethylformamide / 1 h / -10 °C
2: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
3: MsOH / ethanol / 7.5 h / 35 - 40 °C
4: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
5: MsOH / ethanol / 35 - 40 °C
View Scheme
10314-98-4

1-benzyloxycarbonylpiperidine-4-carboxylic acid

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C
2: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr
3: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
4: NaBH4 / toluene / 0.5 h / -2 °C
5: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
6: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
7: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
8: MsOH / ethanol / 7.5 h / 35 - 40 °C
9: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
10: MsOH / ethanol / 35 - 40 °C
View Scheme
138163-08-3

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
2: NaBH4 / toluene / 0.5 h / -2 °C
3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
4: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
5: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
6: MsOH / ethanol / 7.5 h / 35 - 40 °C
7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
8: MsOH / ethanol / 35 - 40 °C
View Scheme
10314-99-5

benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr
2: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
3: NaBH4 / toluene / 0.5 h / -2 °C
4: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
5: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
6: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
7: MsOH / ethanol / 7.5 h / 35 - 40 °C
8: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
9: MsOH / ethanol / 35 - 40 °C
View Scheme
100-63-0

phenylhydrazine

1.4-diphenyl-butanedione-(2.3)

1.4-diphenyl-butanedione-(2.3)

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
2: NaBH4 / toluene / 0.5 h / -2 °C
3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
4: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
5: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
6: MsOH / ethanol / 7.5 h / 35 - 40 °C
7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
8: MsOH / ethanol / 35 - 40 °C
View Scheme
178261-41-1

1-(methylsulfonyl)spiro[indoline-3,4’-piperidine]

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
2: MsOH / ethanol / 7.5 h / 35 - 40 °C
3: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
4: MsOH / ethanol / 35 - 40 °C
View Scheme
184289-85-8

benzyl spiro[indole-3,4'-piperidine]-1'-carboxylate

159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: NaBH4 / toluene / 0.5 h / -2 °C
2: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
3: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
4: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
5: MsOH / ethanol / 7.5 h / 35 - 40 °C
6: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
7: MsOH / ethanol / 35 - 40 °C
View Scheme
Raw Materials
184289-85-8
178261-41-1
10314-99-5
138163-08-3
167484-18-6
47173-80-8
100-63-0
100-39-0
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Specification

The Ibutamoren, with the CAS registry number 159634-47-6, is also known as Propanamide, 2-amino-N-((1R)-2-(1,2-dihydro-1-(methylsulfonyl)spiro(3H-indole-3,4'-piperidin)-1'-yl)-2-oxo-1-((phenylmethoxy)methyl)ethyl)-2-methyl-. This chemical's molecular formula is C27H36N4O5S and molecular weight is 528.67. What's more, its systematic name is 2-amino-2-methyl-N-[(2R)-1-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl]propanamide.

Physical properties of Ibutamoren are: (1)ACD/LogP: 3.53; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.45; (4)ACD/LogD (pH 7.4): 3.1; (5)ACD/BCF (pH 5.5): 2.34; (6)ACD/BCF (pH 7.4): 106.17; (7)ACD/KOC (pH 5.5): 16.37; (8)ACD/KOC (pH 7.4): 742.47; (9)#H bond acceptors: 9; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 98.85 Å2; (13)Index of Refraction: 1.631; (14)Molar Refractivity: 142.65 cm3; (15)Molar Volume: 400 cm3; (16)Polarizability: 56.55×10-24cm3; (17)Surface Tension: 63.4 dyne/cm; (18)Density: 1.32 g/cm3.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(C)(C(=O)NC(COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C)N
(2)Isomeric SMILES: CC(C)(C(=O)N[C@H](COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C)N
(3)InChI: InChI=1S/C27H36N4O5S/c1-26(2,28)25(33)29-22(18-36-17-20-9-5-4-6-10-20)24(32)30-15-13-27(14-16-30)19-31(37(3,34)35)23-12-8-7-11-21(23)27/h4-12,22H,13-19,28H2,1-3H3,(H,29,33)/t22-/m1/s1
(4)InChIKey: UMUPQWIGCOZEOY-JOCHJYFZSA-N