Sodium Hydroxide → N-[(R)-6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-hydroxy-acetamide

HRID 1013603Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C@H:17]([CH2:21][NH:22][C:23]([CH2:25][O:26]C(=O)C)=[O:24])[CH2:16][CH2:15][CH2:14]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C@H:17]([CH2:21][NH:22][C:23](=[O:24])[CH2:25][OH:26])[CH2:16][CH2:15][CH2:14]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Acetic acid {[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl ester (0.1 g) was dissolved in 10 mL methanol, and 2 mL of 2M aqueous NaOH was added. The reaction mixture was heated to 60° C. with stirring for 20 minutes, then cooled and concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate, and the organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. The oily residue was recrystallized from methyl tert-butyl ether/hexanes (1:1) to 80 mg of N—[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-hydroxy-acetamide, MS (M+H)=378.

Workup

temperaturecooled
concentrationconcentrated under reduced pressure
customThe residue was partitioned between water and ethyl acetate
customthe organic layer was separated
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customThe oily residue was recrystallized from methyl tert-butyl ether/hexanes (1:1) to 80 mg of N—[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-hydroxy-acetamide, MS (M+H)=378

Sources & evidence

ORD record: ord-7304277a7ae84ec2a17109bbcf430c28
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981923B2

Reaction notes

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