4-Methoxybenzenesulfonyl chloride → (+/-)-2-[2-(1-Benzyloxymethylpyrimidin-2,4-dione-3-yl)ethyl]-n-(4-methoxy-benzenesulfonyl)glycine allyl ester

HRID 1838412Notes

Reaction equation

HRID 1838412 reaction equation
[CH2:1]([O:4][C:5](=[O:34])[CH:6]([CH2:15][CH2:16][N:17]1[C:22](=[O:23])[CH:21]=[CH:20][N:19]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:18]1=[O:33])[NH:7]C(OC(C)(C)C)=O)[CH:2]=[CH2:3].C(OC(=O)C(CCN1C(=O)C2=CC=CC=C2C1=O)NC(OC(C)(C)C)=O)C=C.[CH3:63][O:64][C:65]1[CH:70]=[CH:69][C:68]([S:71](Cl)(=[O:73])=[O:72])=[CH:67][CH:66]=1>>[CH2:1]([O:4][C:5](=[O:34])[CH:6]([CH2:15][CH2:16][N:17]1[C:22](=[O:23])[CH:21]=[CH:20][N:19]([CH2:24][O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:18]1=[O:33])[NH:7][S:71]([C:68]1[CH:67]=[CH:66][C:65]([O:64][CH3:63])=[CH:70][CH:69]=1)(=[O:73])=[O:72])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 18753523(+/-)-2-[2-(1-Benzyloxymethylpyrimidin-2,4-dione-3-yl)ethyl]-n-(tert-butoxy-carbonyl)glycine allyl ester2×HCID 18753589(+/-)-n-(Tert-butoxycarbonyl)-2-(phthalimidoethyl)glycine allyl ester

Product 1

HCID 18753579(+/-)-2-[2-(1-Benzyloxymethylpyrimidin-2,4-dione-3-yl)ethyl]-n-(4-methoxy-benzenesulfonyl)glycine allyl esterYield 93%

Procedure

In a similar manner to the procedures described in Example 1(2)-a and b, reactions were carried out using (±)-2-[2-(1-benzyloxymethylpyrimidin-2,4-dione-3-yl)ethyl]-N-(tert-butoxycarbonyl)glycine allyl ester, the product of (1) above, instead of (±)-N-(tert-butoxycarbonyl)-2-(2-phthalimidoethyl)glycine allyl ester and using 4-methoxybenzenesulfonyl chloride instead of 4-phenoxybenzenesulfonyl chloride to afford the desired compound (yield 93%) as a colorless oil.

Sources & evidence

ORD record
ord-8ebd91182287466b8da56f07b64a197b
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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