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Synthetic route

: 112507-71-8
13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid hydrazide

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
ueber 6-<6-Amino-hexanoylamino>-hexansaeure-hydrazid-hydrobromid und das entsprechende Azid;
Multi-step reaction with 3 steps 1: 33percent HBr / acetic acid / 1 h / 20 °C 2: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 3: aq. NaHCO3 / 4 h / 20 °C View Scheme

: 2014-58-6
6-(6-aminohexanamido)hexanoic acid

: 541-41-3
chloroformic acid ethyl ester

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
With tributyl-amine

: 6-(6-Amino-hexanoylamino)-hexanoyl azide; hydrobromide

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
With sodium hydrogencarbonate at 20℃; for 4h; Yield given;

: 109565-05-1
6-(6-amino-hexanoylamino)-hexanoic acid-(4-nitro-phenyl ester); hydrobromide

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 60℃; for 4h; Yield given;

: 6-(6-Amino-hexanoylamino)-hexanoic acid 4-nitro-phenyl ester; compound with trifluoro-acetic acid

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Yield given;

6-<6-amino-hexanoylamino>-hexanoic acid <2,4-dinitro-phenyl ester>-hydrobromide: 6-<6-amino-hexanoylamino>-hexanoic acid <2,4-dinitro-phenyl ester>-hydrobromide

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
With tributyl-amine; N,N-dimethyl-formamide

6-<6-amino-hexanoylamino>-hexanoic acid <4-nitro-phenyl ester>-hydrobromide: 6-<6-amino-hexanoylamino>-hexanoic acid <4-nitro-phenyl ester>-hydrobromide

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
With triethylamine; N,N-dimethyl-formamide

6-<6-amino-hexanoylamino>-hexanoyl chloride-hydrochloride: 6-<6-amino-hexanoylamino>-hexanoyl chloride-hydrochloride

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
With triethylamine; N,N-dimethyl-formamide

: 51513-80-5
N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 94 percent / 1,2-dimethoxy-ethane / 3 h 2: 100 percent / H2, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr 3: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 4: 0.25 h / 50 °C 5: Et3N / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: 95 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 2: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 3: 0.25 h / 50 °C 4: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

: 6404-29-1
6-(tert-butoxycarbonylamino)hexanoic acid

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C 2: 94 percent / 1,2-dimethoxy-ethane / 3 h 3: 100 percent / H2, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr 4: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 5: 0.25 h / 50 °C 6: Et3N / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 5 steps 1: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C 2: 95 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 3: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 4: 0.25 h / 50 °C 5: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

: 1947-00-8
6-(benzyloxycarbonylamino)hexanoic acid

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: DCC / dioxane / 24 h / 0 °C 2: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 3: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C 4: 33percent HBr / acetic acid / 2 h / 20 °C 5: pyridine / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 7 steps 1: DCC / dioxane / 24 h / 0 °C 2: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 3: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 4: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 5: 33percent HBr / acetic acid / 1 h / 20 °C 6: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 7: aq. NaHCO3 / 4 h / 20 °C View Scheme

: 49701-55-5
13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C 2: 33percent HBr / acetic acid / 2 h / 20 °C 3: pyridine / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 5 steps 1: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 2: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 3: 33percent HBr / acetic acid / 1 h / 20 °C 4: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 5: aq. NaHCO3 / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine; chlorocarbonic acid ethyl ester; THF / anschliessend Behandeln mit N2H4+H2O in H2O 2: ueber 6-<6-Amino-hexanoylamino>-hexansaeure-hydrazid-hydrobromid und das entsprechende Azid View Scheme

: 25580-88-5
methyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 2: 33percent HBr / acetic acid / 1 h / 20 °C 3: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 4: aq. NaHCO3 / 4 h / 20 °C View Scheme

: 121759-91-9
p-nitrophenyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 33percent HBr / acetic acid / 2 h / 20 °C 2: pyridine / dimethylformamide / 4 h / 60 °C View Scheme

: 53733-98-5
N-hydroxysuccinimide ester of 6-{[(benzyloxy)carbonyl]amino}hexanoic acid

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 2: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C 3: 33percent HBr / acetic acid / 2 h / 20 °C 4: pyridine / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 6 steps 1: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 2: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 3: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 4: 33percent HBr / acetic acid / 1 h / 20 °C 5: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 6: aq. NaHCO3 / 4 h / 20 °C View Scheme

: 14254-45-6
13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoic acid

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 2: 0.25 h / 50 °C 3: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

: 144366-96-1
benzyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / H2, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr 2: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 3: 0.25 h / 50 °C 4: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

: 6-Amino-hexanoic acid (5-hydrazinocarbonyl-pentyl)-amide; hydrobromide

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 2: aq. NaHCO3 / 4 h / 20 °C View Scheme

: 144366-97-2
p-nitrophenyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.25 h / 50 °C 2: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

: 60-32-2
6-aminohexanoic acid

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 83 percent / 4 M NaOH / 4 h / 0 - 20 °C 2: DCC / dioxane / 24 h / 0 °C 3: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 4: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C 5: 33percent HBr / acetic acid / 2 h / 20 °C 6: pyridine / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 8 steps 1: 83 percent / 4 M NaOH / 4 h / 0 - 20 °C 2: DCC / dioxane / 24 h / 0 °C 3: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 4: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 5: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 6: 33percent HBr / acetic acid / 1 h / 20 °C 7: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 8: aq. NaHCO3 / 4 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1: 96 percent / MgO, H2O / dioxane / 26 h / 50 °C 2: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C 3: 94 percent / 1,2-dimethoxy-ethane / 3 h 4: 100 percent / H2, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr 5: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 6: 0.25 h / 50 °C 7: Et3N / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 6 steps 1: 96 percent / MgO, H2O / dioxane / 26 h / 50 °C 2: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C 3: 95 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 4: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 5: 0.25 h / 50 °C 6: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

: 295-29-4
1,8-diazacyclotetradecane

Conditions

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 4h; Heating;	64%
With lithium aluminium tetrahydride

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

aqueous H2SO4 (3 n): aqueous H2SO4 (3 n)

: 60-32-2
6-aminohexanoic acid

Conditions

Conditions	Yield
at 78℃; Rate constant; und 100grad.Hydrolysis;

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

aqueous HCl (7.7 n): aqueous HCl (7.7 n)

: 60-32-2
6-aminohexanoic acid

Conditions

Conditions	Yield
at 110℃; Rate constant; Hydrolysis;

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

: 108880-79-1
1,8-dinitroso-1,8-diaza-cyclotetradecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: aqueous HCl; NaNO2 View Scheme

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

: 109452-16-6
1,8-diacetyl-1,8-diaza-cyclotetradecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 View Scheme

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

: 119276-12-9
1,8-dibenzyl-1,8-diaza-cyclotetradecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: ethanolic KOH View Scheme

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

: 121972-55-2
1,8-dibenzoyl-1,8-diaza-cyclotetradecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: aqueous KOH; THF View Scheme

: 56403-09-9
1,8-diazacyclotetradecane-2,9-dione

: 109600-31-9
1-(2,4-dinitro-phenyl)-1,8-diaza-cyclotetradecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: DMF; H2O / 140 °C View Scheme

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