3-Acetamidopyrrolidine → 7-(3-Benzyloxycarbonylamino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1759554Notes

Reaction equation

HRID 1759554 reaction equation
C(NC1CCNC1)(=O)C.[CH2:10]([O:17][C:18]([NH:20][CH:21]1[CH2:25][CH2:24][NH:23][CH2:22]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl[C:27]1[N:36]=[C:35]2[C:30]([C:31](=[O:42])[C:32]([C:39]([OH:41])=[O:40])=[CH:33][N:34]2[CH2:37][CH3:38])=[CH:29][C:28]=1[F:43]>>[CH2:10]([O:17][C:18]([NH:20][CH:21]1[CH2:25][CH2:24][N:23]([C:27]2[N:36]=[C:35]3[C:30]([C:31](=[O:42])[C:32]([C:39]([OH:41])=[O:40])=[CH:33][N:34]3[CH2:37][CH3:38])=[CH:29][C:28]=2[F:43])[CH2:22]1)=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 5227153-AcetamidopyrrolidineHCID 112067813-N-Cbz-aminopyrrolidineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 205311867-(3-Benzyloxycarbonylamino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Procedure

In place of 3-acetylaminopyrrolidine, 3-benzyloxycarbonylaminopyrrolidine was allowed to react with 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid in the same manner as described in Example 1 to give 7-(3-benzyloxycarbonylamino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, which was used in the next step:

Sources & evidence

ORD record
ord-13b9771948d44a6ea18fa2da5c52ba82
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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