Diethyl Ether → HCID 22851825, compound

HRID 1034449Notes

Reaction equation

CC(=C)C.[O:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[CH:31]([CH3:38])[CH2:30][CH:29]([NH:39][C:40](=[O:50])[CH2:41][C:42]([NH:45][CH2:46][C@H:47]([OH:49])[CH3:48])([CH3:44])[CH3:43])[C:28]3=[O:51])=[CH:22][CH:21]=2)=[O:12])[CH2:7][CH2:6]1.C([O:54]CC)C>>[O:5]1[CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[CH:31]([CH3:38])[CH2:30][CH:29]([NH:39][C:40](=[O:50])[CH2:41][C:42]([NH:45][CH2:46][C@H:47]([OH:49])[CH2:48][OH:54])([CH3:43])[CH3:44])[C:28]3=[O:51])=[CH:22][CH:21]=2)=[O:12])[CH2:7][CH2:6]1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 8255Isobutylene

HCID 22851824HCID 22851824, compound

Product 1

HCID 22851825HCID 22851825, compound

Procedure

Reaction of isobutylene with N-chlorosulfonylisocyanate 57 in diethyl ether gives the azetidinone derivative 58. Removal of the chlorosulfonyl group with aqueous sodium sulfite followed by reaction with di-t-butyl-dicarbonate gives the BOC-protected intermediate 60. Alkaline hydrolysis gives the protected amino acid derivative 61 in good overall yield.

Sources & evidence

ORD record: ord-f384fcf1d6b344c19aab290be3bf04b4
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05317017

Reaction notes

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