Triethylamine → HCID 9821989, compound

HRID 987224Notes

Reaction equation

C([O:3][C:4](=[O:28])[CH2:5][CH:6]([NH:13][C:14]([C:16]1[C:25](=[O:26])[N:24]2[C:19]([CH:20]=[C:21](Cl)[CH:22]=[CH:23]2)=[CH:18][CH:17]=1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.C(NC[CH2:38][CH2:39][NH2:40])(OC(C)(C)C)=O.C([N:43](CC)CC)C>N1C=CC=CC=1>[NH2:43][CH2:38][CH2:39][NH:40][C:21]1[CH:22]=[CH:23][N:24]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:14]([NH:13][CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:5][C:4]([OH:3])=[O:28])=[O:15])[C:25]2=[O:26]

Participants

Conditions

Temperature: 60 °C

Procedure

To solution of (+/−)-3-[(8-Chloro-4-oxo-4H-quinolizine-3-carbonyl)-amino]-3-phenyl-propionic acid ethyl ester (32 mg, 0.080 mmol) in anhydrous pyridine (0.7 ml) at room temperature were sequentially added N-Boc-1,3-diaminopropane (30.9 mg, 0.19 mmol)and triethylamine (31.4 μl, 0.23 mmol). The resulting mixture was heated at 60° C. for 18 h. The solvent was removed under vacuum and the resulting residue subjected to a silica gel chromatography (EtOAc to EtOAc: MeOH=9:1) to give the desired product as yellowish solid (30 mg, 73%)

Workup

customat room temperature
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-520e2720e88b4fad97119f2cdbe123f7
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06630488B1

Reaction notes

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