p-(Trifluoromethoxy)benzenesulphonyl chloride → (+/-)-2-(2-Phthalimidoethyl)-N-(4-trifluoromethoxybenzensulfonyl)glycine Benzyl Ester

HRID 1838418Notes

Reaction equation

HRID 1838418 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.[F:61][C:62]([F:75])([F:74])[O:63][C:64]1[CH:69]=[CH:68][C:67]([S:70]([Cl:73])(=[O:72])=[O:71])=[CH:66][CH:65]=1>>[O:63]([C:64]1[CH:69]=[CH:68][C:67]([S:70]([Cl:73])(=[O:72])=[O:71])=[CH:66][CH:65]=1)[C:62]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:70]([C:67]1[CH:66]=[CH:65][C:64]([O:63][C:62]([F:61])([F:74])[F:75])=[CH:69][CH:68]=1)(=[O:72])=[O:71])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 523102p-(Trifluoromethoxy)benzenesulphonyl 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 18753638(+/-)-2-(2-Phthalimidoethyl)-N-(4-trifluoromethoxybenzensulfonyl)glycine Benzyl EsterYield 52%

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-trifluoromethoxybenzenesulfonyl chloride, instead of 4-phenoxybenzenesulfonyl chloride, to afford the desired compound (yield 52%) as a yellow powder.

Sources & evidence

ORD record
ord-903b3acdbced432f926e223fa9773c5a
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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