N-(4-Bromobutyl)phthalimide → HCID 18416782, compound

HRID 2270324Notes

Reaction equation

C([O:3][C:4](=[O:33])[C:5]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])([CH3:21])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])C.C(OC(=O)CS(C1C=CC(OC)=CC=1)(=O)=O)C.C1(=O)N(CCCCBr)C(=O)C2=CC=CC=C12>>[O:19]=[C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:20])[N:10]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([S:22]([C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)(=[O:23])=[O:24])([CH3:21])[C:4]([OH:33])=[O:3]

Participants

Reactant 3

HCID 93575N-(4-Bromobutyl)phthalimide

HCID 14823722-[(4-Methoxyphenyl)sulfonyl]acetic acid ethyl ester

HCID 54072529HCID 54072529, compound2×

Product 1

HCID 18416782HCID 18416782, compoundYield 88%

Procedure

Following the procedure as outlined in Example 9, 6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-benzenesulfonyl)-2-methyl-hexanoic acid ethyl ester was prepared, starting from (5.0 g, 20 mmol) of 2-(4-methoxy-benzenesulfonyl)-acetic acid ethyl ester and 4-phathalimido bromobutane (5.66 g, 20 mmol). Yield 8.4 g, 97%; Colorless oil; MS: 474 (M+H). Starting from 6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-benzenesulfonyl)-2-methyl-hexanoic acid ethyl ester (8.4 g, 17.7 mmol) 6;95 g (88%) of 6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-benzenesulfonyl)-2-methyl-hexanoic acid was isolated as colorless oil by following the procedure as outlined in Example 9. MS: 446 (M−H)−.

Workup

customwas prepared

Sources & evidence

ORD record: ord-e29271f6f0fb4368af6fec7b30154654
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331563B1

Reaction notes

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