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80474-45-9

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Basic Information
CAS No.: 80474-45-9
Name: FLUTICASONE PROPIONATE INTERMEDIATE
Article Data: 16
Molecular Structure:
Molecular Structure of 80474-45-9 (FLUTICASONE PROPIONATE INTERMEDIATE)
Formula: C24H30F2O5S
Molecular Weight: 468.562
Synonyms: FLUTICASONE PROPIONATE INTERMEDIATE;6,9-DIFLUORO-11B-HYRDOXY-16-METHYL-3-OXO-17-PROPIONYLOXYANDROSTA-1,4-DIENE-17B-CARBPTHIOCACID;(6alpha,11beta,,16alpha,17alpha)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxo-propoxy)androsta-1,4-diene-17-carbothioic acid;6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-;Androsta-1,4-diene-17-carbothioic acid;oxopropoxy)-, (6α,11β,16α,17α)-;6a,9a-difluoro-l1~-hydroxy-l6a-methyl- 17a-propionyloxy-3-oxoandrosta-l,4-diene-l7~-carbothioic acid;(6a,11b,16a,17a)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-androsta-1,4-diene-17-carbothioic acid
Density: 1.315 g/cm3
Melting Point: 158-160 °C
Boiling Point: 563.337 °C at 760 mmHg
Flash Point: 294.496 °C
Solubility: 50mg/L at 20℃
Appearance: white solid
PSA: 119.47000
LogP: 3.69960
Related products
Synthetic route
105638-31-1

17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
Stage #1: 17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene With methanol; potassium carbonate at 20℃; for 5 - 7h;
Stage #2: With hydrogenchloride In water at 20℃; pH=1.5 - 2.0; Product distribution / selectivity;		96.33%
With calcium hydroxide In methanol at 25 - 30℃; for 24h; Reagent/catalyst;96.3%
With potassium carbonate In methanol at 25℃; for 5h; Inert atmosphere;95%
79-03-8

propionyl chloride

80473-92-3

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
Stage #1: propionyl chloride; 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid With triethylamine In dichloromethane at -5℃;
Stage #2: With diethylamine In acetone for 1h; regioselective reaction;		91%
With pyridine In acetone at -20 - -15℃; Product distribution / selectivity;88%
With 1-methyl-1H-imidazole In acetone at -20 - -15℃; Product distribution / selectivity;88%
65429-42-7

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
Stage #1: 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid With 1-methyl-1H-imidazole In ISOPROPYLAMIDE at 50℃;
Stage #2: With sodium hydrogensulfide In ISOPROPYLAMIDE at 35℃; for 0.25h;
Stage #3: With hydrogenchloride In ISOPROPYLAMIDE; water pH=2;		32%
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2 / 20 °C
2: Et2NH / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C
2: morpholine / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine; sodium iodide / acetone; water / 6 h / 10 - 30 °C
1.2: 1 h / 0 °C
2.1: potassium carbonate / methanol / 5 h / 25 °C / Inert atmosphere
View Scheme
577965-09-4

Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propionylsulfanylcarbonyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
With diethylamine In acetone for 1h; Yield given;
578740-28-0

C24H29F2O5S(1-)*K(1+)

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; pH=1 - 2;
80473-92-3

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2 / 0.75 h
2: Et2NH / acetone / 1 h
View Scheme
28416-82-2

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dimethylformamide / 4 h / Ambient temperature
2: H2S / dimethylformamide
3: Et3N / CH2Cl2 / 0.75 h
4: Et2NH / acetone / 1 h
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / acetone / 3 h / 0 - 5 °C
1.2: 2.5 h / 40 - 45 °C
2.1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C
3.1: morpholine / 3 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / acetone / 4 h / 10 - 25 °C
1.2: 10 - 25 °C
1.3: 0 °C / pH 1 - 1.5
2.1: triethylamine; sodium iodide / acetone; water / 6 h / 10 - 30 °C
2.2: 1 h / 0 °C
3.1: potassium carbonate / methanol / 5 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / acetone / 1 h / 0 - 10 °C
1.2: 2 h
2.1: sodium iodide; triethylamine / tetrahydrofuran / 16 h / 20 °C
3.1: calcium hydroxide / methanol / 24 h / 25 - 30 °C
View Scheme

(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-Difluoro-11,17-dihydroxy-17-(imidazole-1-carbonyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2S / dimethylformamide
2: Et3N / CH2Cl2 / 0.75 h
3: Et2NH / acetone / 1 h
View Scheme

C28H33F2NO8

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
With sodium hydrogensulfide In ISOPROPYLAMIDE at 35℃; for 0.25h;
105638-31-1

17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene

A

59860-80-9

methyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carboxylate

B

80474-45-9

17-propionate carbothioic acid

Conditions
ConditionsYield
With methanol; potassium carbonate at 20℃; for 1 - 5h; Product distribution / selectivity;
With methanol; caesium carbonate at 20℃; for 1 - 5h; Product distribution / selectivity;
Raw Materials
65429-42-7
79-03-8
109-89-7
28416-82-2
80473-92-3
105638-31-1
1892-31-5
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80474-14-2
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Specification

The (6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-androsta-1,4-diene-17-carbothioic acid, with the CAS registry number 80474-45-9, is also known as Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, (6α,11β,16α,17α)-. This chemical's molecular formula is C24H30F2O5S and molecular weight is 468.5538. Its systematic name is called (6α,11β,16α,17α)-6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(propanoyloxy)androsta-1,4-diene-17-carbothioic S-acid.

Physical properties of (6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-androsta-1,4-diene-17-carbothioic acid: (1)ACD/LogP: 2.67; (2)ACD/LogD (pH 7.4): -1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 3; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 5; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.566; (11)Molar Refractivity: 116.238 cm3; (12)Molar Volume: 356.34 cm3; (13)Surface Tension: 49.269 dyne/cm; (14)Density: 1.315 g/cm3; (15)Flash Point: 294.496 °C; (16)Enthalpy of Vaporization: 97.273 kJ/mol; (17)Boiling Point: 563.337 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(S)[C@]3(OC(=O)CC)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)C[C@H]4[C@@H]2C[C@H]3C)C)C
(2)InChI: InChI=1/C24H30F2O5S/c1-5-19(29)31-24(20(30)32)12(2)8-14-15-10-17(25)16-9-13(27)6-7-21(16,3)23(15,26)18(28)11-22(14,24)4/h6-7,9,12,14-15,17-18,28H,5,8,10-11H2,1-4H3,(H,30,32)/t12-,14+,15+,17+,18+,21+,22+,23+,24+/m1/s1
(3)InChIKey: QGESYFOFLPJDJW-CQRCZTONBZ