Boron tribromide → 3-(Biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxylic acid

HRID 1964805Notes

Reaction equation

[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][CH2:13][S:12][CH:11]2[C:15]([O:17]C)=[O:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][CH2:13][S:12][CH:11]2[C:15]([OH:17])=[O:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution was made containing Intermediate 6, e.g., methyl 3-([1,1′-biphenyl]-4-ylsulfonyl)-1,3-thiazolidine-2-carboxylate (2.0 g, 5.5 mmol, 1 eq), in dry DCM (50 ml). The flask was cooled down to −20° C. in a dry-acetone bath. A solution of boron tribromide (5.55 g, 22.0 mmol) in dry DCM (30 ml) was added drop wise over a period of 10 minutes. The reaction mixture was stirred for 1 h at 0° C. The reaction mixture was diluted with DCM (50 ml) and washed with a 1M HCl solution (2×50 ml) and with brine (50 ml) before drying over magnesium sulfate, filtering and removal of solvent in vacuo. The desired product of general structure (VIII), e.g., 3-([1,1′-biphenyl]-4-ylsulfonyl)-1,3-thiazolidine-2-carboxylic acid, was isolated as a white powder (1.8 g, 94%).

Workup

customa dry-acetone bath
washwashed with a 1M HCl solution (2×50 ml) and with brine (50 ml)
dry with materialbefore drying over magnesium sulfate
filtrationfiltering
customremoval of solvent in vacuo

Sources & evidence

ORD record: ord-9feb26d5199e40beada0f04a5aad60b7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415480B2

Reaction notes

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