HCID 18992037, compound → HCID 56610338, compound

HRID 375743Notes

Reaction equation

Br[CH2:2][C:3]1[C:21]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:20][C:19]([O:30][CH3:31])=[CH:18][C:4]=1[C:5](OCC1C=CC([N+]([O-])=O)=CC=1)=[O:6].[OH:32][C@@H:33]([C:45]([O:47][CH3:48])=[O:46])[CH2:34][C:35]([NH:37][C@@H:38]([CH2:43][SH:44])[C:39]([O:41][CH3:42])=[O:40])=[O:36]>>[Si:23]([O:22][C:21]1[C:3]2[CH2:2][S:44][CH2:43][C@@H:38]([C:39]([O:41][CH3:42])=[O:40])[NH:37][C:35](=[O:36])[CH2:34][C@@H:33]([C:45]([O:47][CH3:48])=[O:46])[O:32][C:5](=[O:6])[C:4]=2[CH:18]=[C:19]([O:30][CH3:31])[CH:20]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25]

Participants

Reactant 2

HCID 18992037HCID 18992037, compound

HCID 53687195HCID 53687195, compound

Product 1

HCID 56610338HCID 56610338, compound

Procedure

p-Nitrobenzyl 2-bromomethyl-3-(tert-butyldimethylsilyloxy)-5-methoxybenzoate was reacted with methyl (R)-2-[(R)-3-hydroxy-3-methoxycarbonyl-propionylamino]-3-mercapto-propionate in an analogous manner to the procedure described in Example 1(f), and the product was subjected in an analogous manner to a sequence of procedures described in Example 13(f) and in Example 21 to yield dimethyl (4R, 8S)-14-(tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8,10-octahydro-12-methoxy-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-4,8-dicarboxylate as a white solid. This material was treated with ammonium fluoride in methanol in an analogous manner to the procedure described in Example 13 to yield, after crystallization from ethyl acetate/hexane, dimethyl (4R, 8S)-1,3,4,5,6,7,8,10-octahydro-14-hydroxy-12-methoxy-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-4,8-dicarboxylate as a white solid.

Sources & evidence

ORD record: ord-c232883ad82e4d66a52be6d05602b206
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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