HCID 21271729, compound → HCID 21271728, compound

HRID 1194112Notes

Reaction equation

C[O:2][C:3](=[O:30])[C:4]([CH3:29])([CH3:28])[CH2:5][CH2:6][N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([S:17](=[O:27])(=[O:26])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:12][CH:13]=2)[CH2:8]1.O=C(N1CCC2C(=CC(S(=O)(=O)NC3C=CC=C(Cl)C=3)=CC=2)C1)C(C)(C)CCN1CCC2C(=CC(S(=O)(=O)NC3C=CC=C(Cl)C=3)=CC=2)C1>>[CH3:28][C:4]([CH3:29])([CH2:5][CH2:6][N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([S:17](=[O:27])(=[O:26])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:12][CH:13]=2)[CH2:8]1)[C:3]([OH:30])=[O:2]

Participants

Reactant 2

HCID 21271729HCID 21271729, compound

HCID 21271740HCID 21271740, compound

Product 1

HCID 21271728HCID 21271728, compound

Procedure

Following the method of Example 2(a), substituting methyl-2,2-dimethyl-4-bromobutanoate (J. L. Bass et al, Tetrahedron, 1966, 22, 285) gave a mixture of methyl-2,2-dimethyl-4-[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]butanoate and 1-oxo-2,2-dimethyl-1,4-bis-[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]butane, which were separated by chromatography (silica gel, ether). The former compound was hydrolysed by the method of Example 2(b), substituting methanol for ethanol and carrying out the reaction for 24 hours, to give, after recrystallisation from ethanol, 2,2-dimethyl-4-[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]butanoic acid, 1.1 C2H5OH, 0.8 H2O, m.p. ca. 120° C.

Workup

customgave
customwere separated by chromatography (silica gel, ether)
customthe reaction for 24 hours
customto give
customafter recrystallisation from ethanol, 2,2-dimethyl-4-[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]butanoic acid, 1.1 C2H5OH, 0.8 H2O, m.p. ca. 120° C.

Sources & evidence

ORD record: ord-d056ba474b8c4e4893361d04b5a26add
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812573

Reaction notes

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