(+/-)-N-(tert-butoxycarbonyl)homoserine allyl ester → (+/-)-2-[2-(1-Benzyloxymethylpyrimidin-2,4-dione-3-yl)ethyl]-n-(tert-butoxycarbonyl)glycine benzyl ester

HRID 1838413Notes

Reaction equation

HRID 1838413 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[C@H:10]([CH2:19][CH2:20]O)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)[C@H](CCO)[NH:29][C:30](OC(C)(C)C)=[O:31])C=C.[CH2:41]([O:48][CH2:49][N:50]1[CH:55]=[CH:54][C:53](=[O:56])[NH:52][C:51]1=[O:57])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[C:30]1(=[O:31])[NH:29][C:1](=[O:8])[C:2]2=[CH:3][CH:4]=[CH:5][CH:6]=[C:7]12.[CH2:1]([O:8][C:9](=[O:22])[CH:10]([CH2:19][CH2:20][N:52]1[C:53](=[O:56])[CH:54]=[CH:55][N:50]([CH2:49][O:48][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:51]1=[O:57])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12042107(+/-)-N-(tert-butoxycarbonyl)homoserine allyl esterHCID 130164351-((benzyloxy)methyl)pyrimidine-2,4(1H,3H)-dioneHCID 13970788HCID 13970788, compound

Product 2

HCID 6809PhthalimideHCID 18753538(+/-)-2-[2-(1-Benzyloxymethylpyrimidin-2,4-dione-3-yl)ethyl]-n-(tert-butoxycarbonyl)glycine benzyl esterYield 74%

Procedure

In a similar manner to that described in Example 1(1), a reaction was carried out using (±)-N-(tert-butoxycarbonyl)homoserine benzyl ester, instead of (±)-N-(tert-butoxycarbonyl)homoserine allyl ester, and using 1-benzyloxymethylpyrimidine-2,4-dione, instead of phthalimide, to afford the desired compound (yield 74%) as a pale yellow oil.

Sources & evidence

ORD record
ord-57ddea7013e6437d8c0b3eb718756c05
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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