Glycosmicine → (+/-)-N-Methyl-2-[2-(1-methylquinazolin-2,4-dione-3-yl]ethyl)-N-(4-phenoxybenzenesulfonyl)glycine Allyl Ester

HRID 1838424

Reaction equation

HRID 1838424 reaction equation
[CH2:1]([O:4][C:5](=[O:28])[CH:6]([CH2:25][CH2:26]O)[N:7]([CH3:24])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH:2]=[CH2:3].C(OC(=O)[C@H](CCO)NC(OC(C)(C)C)=O)C=C.[CH3:47][N:48]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:51](=[O:58])[NH:50][C:49]1=[O:59]>>[C:51]1(=[O:58])[NH:50][C:49](=[O:59])[C:57]2=[CH:56][CH:55]=[CH:54][CH:53]=[C:52]12.[CH2:1]([O:4][C:5](=[O:28])[CH:6]([CH2:25][CH2:26][N:50]1[C:51](=[O:58])[C:52]2[C:57](=[CH:56][CH:55]=[CH:54][CH:53]=2)[N:48]([CH3:47])[C:49]1=[O:59])[N:7]([CH3:24])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH:2]=[CH2:3]

Participants

5

Procedure

In a similar manner to that described in Example 1(1), a reaction was carried out using (±)-2-(2-hydroxyethyl)-N-methyl-N-(4-phenoxybenzenesulfonyl)glycine allyl ester, the product of Example 41(2), instead of (±)-N-(tert-butoxycarbonyl)homoserine allyl ester, and using 1-methylquinazoline-2,4-dione, instead of phthalimide, to afford the desired compound (yield 72%) as a white powder.

Sources & evidence

ORD record
ord-aa14fb575da14ca08bfc7168fe232b3e
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Linked notes

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