HCID 18992109, compound → tert-butyl (4R, 7R)-1,3,4,5,6,7,8,10-octa-hydro-14-hydroxy-12-methoxy-4-methoxycarbonyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate

HRID 375739Notes

Reaction equation

HRID 375739 reaction equation
Br[CH2:2][C:3]1[C:21]([O:22][Si](C(C)(C)C)(C)C)=[CH:20][C:19]([O:30][CH3:31])=[C:18]([CH3:32])[C:4]=1[C:5](OCC1C=CC([N+]([O-])=O)=CC=1)=[O:6].[CH3:33][O:34][C:35](=[O:53])[C@H:36]([CH2:51][SH:52])[NH:37][C:38](=[O:50])[C@@H:39]([CH2:48][OH:49])[NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>>[OH:22][C:21]1[C:3]2[CH2:2][S:52][CH2:51][C@@H:36]([C:35]([O:34][CH3:33])=[O:53])[NH:37][C:38](=[O:50])[C@H:39]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:45])[CH3:46])=[O:42])[CH2:48][O:49][C:5](=[O:6])[C:4]=2[C:18]([CH3:32])=[C:19]([O:30][CH3:31])[CH:20]=1

Participants

3

Reactant 2

HCID 18992109HCID 18992109, compoundHCID 53744746N-[N-(tert-butoxycarbonyl)-D-seryl]-L-cysteine methyl ester

Product 1

HCID 15973729tert-butyl (4R, 7R)-1,3,4,5,6,7,8,10-octa-hydro-14-hydroxy-12-methoxy-4-methoxycarbonyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate

Procedure

Crude p-nitrobenzyl 2-bromomethyl-3-(tert-butyldimethylsilyloxy)-5-methoxy-6-methylbenzoate, as obtained in Example 23 (d), was reacted with N-[N-(tert-butoxycarbonyl)-D-seryl]-L-cysteine methyl ester in an analogous manner to the procedure described in Example 1 (f), and the product was subjected in an analogous manner to the sequence of procedures used in Example 23 to yield tert-butyl (4R, 7R)-1,3,4,5,6,7,8,10-octa-hydro-14-hydroxy-12-methoxy-4-methoxycarbonyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white solid.

Sources & evidence

ORD record
ord-008cce16fa24482896eee9a4964be44f
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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