HCID 18992037, compound → HCID 53695066, compound

HRID 375742Notes

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]([O:7]CC1C=CC([N+]([O-])=O)=CC=1)=[O:6].[CH3:32][O:33][C:34](=[O:53])[C@H:35]([CH2:51][SH:52])[NH:36][C:37](=[O:50])[C@@H:38]([C@H:47]([CH3:49])O)[NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>>[Si:23]([O:22][C:21]1[C:3]2[CH2:2][S:52][CH2:51][C@@H:35]([C:34]([O:33][CH3:32])=[O:53])[NH:36][C:37](=[O:50])[C@H:38]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@@H:47]([CH3:49])[O:7][C:5](=[O:6])[C:4]=2[CH:18]=[C:19]([O:30][CH3:31])[CH:20]=1)([C:26]([CH3:29])([CH3:27])[CH3:28])([CH3:25])[CH3:24]

Participants

Reactant 2

HCID 18992037HCID 18992037, compound

HCID 53866905HCID 53866905, compound

Product 1

HCID 53695066HCID 53695066, compound

Procedure

p-Nitrobenzyl 2-bromomethyl-3-(tert-butyldimethylsilyloxy)-5-methoxybenzoate was reacted with N-[N-(tert-butoxycarbonyl)-D-threonyl]-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 a sequence of procedures described in Example 13 (f) and in Example 21 to yield tert-butyl (4R, 7R, 8R)-14-(tert-butyldimethylsilyloxy)-1,3,4,5,6, 7,8,10-octahydro-12-methoxy-4-methoxycarbonyl-8-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as white crystals. 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 methanol/diethylether/hexane, tert-butyl (4R, 7R, 8R)-1,3,4,5,6,7,8,10-octahydro- 14-hydroxy-12-methoxy-4-methoxycarbonyl-8-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white solid.

Sources & evidence

ORD record: ord-9a90a16d90bf4ee5b1f585a4c5545c4d
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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