Dichloromethane → HCID 69330970, compound

HRID 2299695Notes

Reaction equation

C([O:5][C:6](=[O:36])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][CH:15]([NH:19][CH2:20][C@H:21]([OH:34])[C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:23]=3)[CH2:14][C:13]=2[CH:35]=1)(C)(C)C.FC(F)(F)C(O)=O.[Cl:44]CCl>>[ClH:44].[OH:34][C@H:21]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:23]=1)[CH2:20][NH:19][CH:15]1[CH2:14][C:13]2[CH:35]=[C:9]([O:8][CH2:7][C:6]([OH:36])=[O:5])[CH:10]=[CH:11][C:12]=2[CH2:18][CH2:17][CH2:16]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 54331878HCID 54331878, compound

Product 1

HCID 69330970HCID 69330970, compound

Procedure

Under nitrogen, to a solution of 2-[8-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylaminophenyl)ethylamino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid tert-butyl ester (257 mg) in dichloromethane (5 ml) was added trifluoroacetic acid (1 ml) at 5° C., and the mixture was stirred at room temperature for 3 hours. The resulting mixture was evaporated in vacuo. The residue was treated with 4N hydrogen chloride in 1,4-dioxane to give 2-[8-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylaminophenyl)ethylamino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid hydrochloride (247 mg).

Workup

customThe resulting mixture was evaporated in vacuo
additionThe residue was treated with 4N hydrogen chloride in 1,4-dioxane

Sources & evidence

ORD record: ord-a1696f8a2c664b2f84cc2d23a916f808
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495546B1

Reaction notes

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