Diethyl Ether → HCID 22850195, compound

HRID 1974586Notes

Reaction equation

HRID 1974586 reaction equation
CC(=C)C.[CH3:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[C:29]3[CH:30]=[CH:31][C:32]([C:34]([F:37])([F:36])[F:35])=[CH:33][C:28]=3[CH2:27][CH2:26][C@@H:25]([NH:38][C:39](=[O:45])[CH2:40][C:41]([NH2:44])([CH3:43])[CH3:42])[C:24]2=[O:46])=[CH:18][CH:17]=1)=[O:8].[CH2:47]([O:49][CH2:50]C)[CH3:48]>>[O:49]1[CH2:47][CH2:48][N:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:17]=[CH:18][C:19]([CH2:22][N:23]3[C:29]4[CH:30]=[CH:31][C:32]([C:34]([F:36])([F:37])[F:35])=[CH:33][C:28]=4[CH2:27][CH2:26][C@@H:25]([NH:38][C:39](=[O:45])[CH2:40][C:41]([NH2:44])([CH3:43])[CH3:42])[C:24]3=[O:46])=[CH:20][CH:21]=2)=[O:8])[CH2:5][CH2:50]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 8255IsobutyleneHCID 22850183HCID 22850183, compound

Product 1

HCID 22850195HCID 22850195, compound

Procedure

Reaction of isobutylene with N-chlorosulfonylisocyanate 37 in diethyl ether gives the azetidinone derivative 38. Removal of the chlorosulfonyl group with aqueous sodium sulfite followed by reaction with di-t-butyl-dicarbonate gives the BOC-protected intermediate 40. Alkaline hydrolysis gives the protected amino acid derivative 41 in good overall yield.

Sources & evidence

ORD record
ord-2ea9d0e25efc4e8ca451c79e8f8a8d0e
Source dataset
uspto-grants-1994_02
Patent number
US05283241

Reaction notes

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