HCID 58597254, compound → HCID 58597292, compound

HRID 1444709Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (R)-(3-nitro-5-(2,2,2-trifluoroacetamido)-5,6,7,8-tetrahydronaphthalen-2-yl)methyl acetate (17 mg) in 10 mL of MeOH was added one drop of 96% H2SO4 and the resulting mixture was stirred at 50° C. for 3 h. After cooling to RT, the reaction was quenched with Sat. NaHCO3 (0.5 mL). The MeOH was evaporated and the residue was directly loaded on column chomatography (SiO2, DCM to DCM/EtOAc=2:1 to 1:1) to give (R)-2,2,2-trifluoro-N-(6-(hydroxymethyl)-7-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)acetamide as a white solid.

Workup

temperatureAfter cooling to RT
customthe reaction was quenched with Sat. NaHCO3 (0.5 mL)
customThe MeOH was evaporated

Sources & evidence

ORD record: ord-4734ed865e024a079c1fc5610ba95d64
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662811B2

Reaction notes

Loading…