Methanol → HCID 53826391, compound

HRID 1607565Notes

Reaction equation

COC(=O)[C:4]1[CH:9]=[CH:8]C=C[C:5]=1[CH2:10][N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([S:21](=[O:31])(=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)=[CH:16][CH:17]=2)[CH2:12]1.[CH3:33][O:34][C:35](=[O:44])C1C=CC=CC=1CBr.C[OH:46]>>[CH3:33][O:34][C:35]([C:8]1[O:46][C:5]([CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([S:21](=[O:30])(=[O:31])[NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)=[CH:16][CH:17]=3)[CH2:12]2)=[CH:4][CH:9]=1)=[O:44]

Participants

Reactant 3

HCID 887Methanol

HCID 2734813Methyl 2-(bromomethyl)benzoate

HCID 19850838HCID 19850838, compound

Product 1

HCID 53826391HCID 53826391, compoundYield 62%

Procedure

Following the procedure of Example 1 to methyl-2-[[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methyl]benzoate, substituting methyl-5-(chloromethyl)-2-furoate (1.75 g, 10 mmol) for methyl-2-(bromomethyl)benzoate and using corresponding proportions of other reagents, gave methyl-5-[[7-(3-chlorophenylsulphamoyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methyl]-2-furoate (2.86 g, 62%), m.pt. 167°-168° C. (from methanol).

Sources & evidence

ORD record: ord-ba8b2dd794934b658e14b75ae2431c33
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04866076

Reaction notes

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