4-(4-Pyridyloxy)benzenesulfonyl chloride → (+/-)-2-(2-Phthalimidoethyl)-N-[4-(pyridin-4-yl)oxybenzensulfonyl]glycine Benzyl Ester

HRID 1838416Notes

Reaction equation

HRID 1838416 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[CH:10]([CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C(CCN1C(=O)C2=CC=CC=C2C1=O)NC(OC(C)(C)C)=O)C=C.[N:61]1[CH:66]=[CH:65][C:64]([O:67][C:68]2[CH:73]=[CH:72][C:71]([S:74]([Cl:77])(=[O:76])=[O:75])=[CH:70][CH:69]=2)=[CH:63][CH:62]=1>>[O:67]([C:68]1[CH:73]=[CH:72][C:71]([S:74]([Cl:77])(=[O:76])=[O:75])=[CH:70][CH:69]=1)[C:64]1[CH:65]=[CH:66][CH:1]=[CH:62][CH:63]=1.[CH2:1]([O:8][C:9](=[O:32])[CH:10]([CH2:19][CH2:20][N:21]1[C:22](=[O:31])[C:23]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]2[C:25]1=[O:26])[NH:11][S:74]([C:71]1[CH:70]=[CH:69][C:68]([O:67][C:64]2[CH:65]=[CH:66][N:61]=[CH:62][CH:63]=2)=[CH:73][CH:72]=1)(=[O:75])=[O:76])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 27352584-(4-Pyridyloxy)benzenesulfonyl chlorideHCID 18753535(+/-)-N-(tert-butoxycarbonyl)-2-(2-phthalimidoethyl)glycine benzyl esterHCID 18753589(+/-)-n-(Tert-butoxycarbonyl)-2-(phthalimidoethyl)glycine allyl ester

Product 2

HCID 27947564-Phenoxybenzene-1-sulfonyl chlorideHCID 18753492(+/-)-2-(2-Phthalimidoethyl)-N-[4-(pyridin-4-yl)oxybenzensulfonyl]glycine Benzyl EsterYield 13%

Procedure

In a similar manner to the procedures described in Example 1(2)-a and b, reactions were carried out using (±)-N-(tert-butoxycarbonyl)-2-(2-phthalimidoethyl)glycine benzyl ester, instead of (±)-N-(tert-butoxycarbonyl)-2-(2-phthalimidoethyl)glycine allyl ester, and using 4-(pyridin-4-yl)oxybenzensulfonyl chloride, instead of 4-phenoxybenzenesulfonyl chloride, to afford the desired compound (yield 13%) as a white amorphous solid.

Sources & evidence

ORD record
ord-440321c1d5574269ac3e247a7f65a465
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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