4-Methoxybenzenesulfonyl chloride → (+/-)-n-(4-Methoxybenzensulfonyl)-2-(2-phthalimidoethyl)glycine benzyl ester

HRID 1838417Notes

Reaction equation

HRID 1838417 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.[CH3:61][O:62][C:63]1[CH:68]=[CH:67][C:66]([S:69]([Cl:72])(=[O:71])=[O:70])=[CH:65][CH:64]=1>>[O:62]([C:63]1[CH:64]=[CH:65][C:66]([S:69]([Cl:72])(=[O:71])=[O:70])=[CH:67][CH:68]=1)[C:61]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=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:69]([C:66]1[CH:65]=[CH:64][C:63]([O:62][CH3:61])=[CH:68][CH:67]=1)(=[O:71])=[O:70])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl 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 18753621(+/-)-n-(4-Methoxybenzensulfonyl)-2-(2-phthalimidoethyl)glycine benzyl esterYield 61%

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, the product of Example 19(1), 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 61%) as a white powder.

Sources & evidence

ORD record
ord-6a4bcca7f72540108fc0900940156fcd
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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