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361441-97-6

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Basic Information
CAS No.: 361441-97-6
Name: (S) - N- Boc- adamantylglycine
Article Data: 6
Molecular Structure:
Molecular Structure of 361441-97-6 ((S) - N- Boc- adamantylglycine)
Formula: C17H27NO4
Molecular Weight: 309.406
Synonyms: (S) - N- Boc- adamantylglycine
Density: 1.193 g/cm3
Melting Point: >300 °C (decomp)(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
Boiling Point: 460.324 °C at 760 mmHg
Flash Point: 232.196 °C
PSA: 79.12000
LogP: 3.38510
Related products
Synthetic route
24424-99-5

di-tert-butyl dicarbonate

102502-64-7

(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 19h;92%
With triethylamine In methanol80%
Stage #1: (S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride With sodium hydroxide In water at 0 - 5℃; for 0.25h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 5℃;		80 g
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere;4.07 g

C17H27NO3

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene In tert-butyl alcohol at 0 - 10℃; for 19.5h;82%
24424-99-5

di-tert-butyl dicarbonate

95853-35-3

(S)-(+)-β-amino-1-adamantaneacetic acid

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 19h;4.07 g
361441-95-4

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
2: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
3: 4.07 g / K2CO3 / dimethylformamide / 19 h
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride; water / acetic acid / 80 °C
2: hydrogen; palladium 10% on activated carbon / acetic acid
3: triethylamine / methanol
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
2.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
3.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
2: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
3: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
View Scheme

(R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
2: 4.07 g / K2CO3 / dimethylformamide / 19 h
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; palladium 10% on activated carbon / acetic acid
2: triethylamine / methanol
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
2.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
2.2: 0 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
2: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
View Scheme
770-71-8

1-adamantanemethanol

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
2: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
3: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
4: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
5: 4.07 g / K2CO3 / dimethylformamide / 19 h
View Scheme
Multi-step reaction with 5 steps
1.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
1.2: 0 - 5 °C
2.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
3.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
4.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
5.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
5.2: 0 - 5 °C
View Scheme
Multi-step reaction with 5 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
2.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
3.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
4.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
5.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
View Scheme
828-51-3

1-Adamantanecarboxylic acid

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / diethyl ether; hexane; methanol / 3 h / 20 °C
2: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
3: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
4: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
5: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
6: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
7: 4.07 g / K2CO3 / dimethylformamide / 19 h
View Scheme
Multi-step reaction with 7 steps
1.1: thionyl chloride / 3 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
4.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
5.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
6.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
7.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
7.2: 0 - 5 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; diethyl ether; hexane / 3 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
3.2: 0.5 h / -78 °C / Inert atmosphere
4.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
5.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
6.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
7.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
View Scheme
2094-74-8

1-Adamantanecarbaldehyde

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
2: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
3: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
4: 4.07 g / K2CO3 / dimethylformamide / 19 h
View Scheme
Multi-step reaction with 4 steps
1: sodium hydrogensulfite / 0 - 60 °C
2: hydrogenchloride; water / acetic acid / 80 °C
3: hydrogen; palladium 10% on activated carbon / acetic acid
4: triethylamine / methanol
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
2.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
3.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
4.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
4.2: 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
2: hydrogenchloride; water / acetic acid / 18 h / 80 °C
3: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
4: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
View Scheme
711-01-3

methyl adamantane-1-carboxylate

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
2: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
3: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
4: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
5: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
6: 4.07 g / K2CO3 / dimethylformamide / 19 h
View Scheme
Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
2.2: 0 - 5 °C
3.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
4.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
5.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
6.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
6.2: 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
3.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
4.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
5.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
6.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
View Scheme

L-boroPro-pn

361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

C31H49BN2O5

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃;93%
Raw Materials
828-51-3
711-01-3
2094-74-8
770-71-8
95853-35-3
24424-99-5
361441-95-4
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361442-01-5
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Specification

The (S)-Adamantylglycine is an organic compound with the formula C17H27NO4. The systematic name of this chemical is (2S)-[(tert-butoxycarbonyl)amino](tricyclo[3.3.1.1~3,7~]dec-1-yl)ethanoic acid. With the CAS registry number 361441-97-6, it is also named as N-Boc-L-Adamantylglycine.

Physical properties about (S)-Adamantylglycine are: (1)ACD/LogP: 3.80; (2)#H bond acceptors: 5; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 5; (5)Polar Surface Area: 75.63 Å2; (6)Index of Refraction: 1.54; (7)Molar Refractivity: 81.419 cm3; (8)Molar Volume: 259.315 cm3; (9)Polarizability: 32.277×10-24cm3; (10)Surface Tension: 48.088 dyne/cm; (11)Density: 1.193 g/cm3; (12)Flash Point: 232.196 °C; (13)Enthalpy of Vaporization: 79.007 kJ/mol; (14)Boiling Point: 460.324 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)(C)C)N[C@H](C(=O)O)C13CC2CC(CC(C1)C2)C3
(2)InChI: InChI=1/C17H27NO4/c1-16(2,3)22-15(21)18-13(14(19)20)17-7-10-4-11(8-17)6-12(5-10)9-17/h10-13H,4-9H2,1-3H3,(H,18,21)(H,19,20)/t10?,11?,12?,13-,17?/m1/s1
(3)InChIKey: LJUATQZYDYSZPV-CQCMJFKXBN
(4)Std. InChI: InChI=1S/C17H27NO4/c1-16(2,3)22-15(21)18-13(14(19)20)17-7-10-4-11(8-17)6-12(5-10)9-17/h10-13H,4-9H2,1-3H3,(H,18,21)(H,19,20)/t10?,11?,12?,13-,17?/m1/s1
(5)Std. InChIKey: LJUATQZYDYSZPV-CQCMJFKXSA-N