Sulfamic Acid → HCID 66612055, compound

HRID 2204710Notes

Reaction equation

[CH:1]([C:3]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[C:5]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:4]=1)=[O:2].S(=O)(=O)([OH:33])N.CC(CC)=C.Cl([O-])=O.[Na+]>O1CCCC1.O.CS(C)=O>[C:25]1([CH2:24][O:23][C:5]2[C:6]([C:7]([O:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:8])=[CH:17][C:18]([C:19]([F:22])([F:20])[F:21])=[C:3]([CH:4]=2)[C:1]([OH:33])=[O:2])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of phenylmethyl 4-formyl-2-[(phenylmethyl)oxy]-5-(trifluoromethyl)benzoate (may be prepared as described in Description 54; 80 mg, 0.19 mmol) in tetrahydrofuran (4 ml), water (2 ml) and dimethyl sulfoxide (0.4 ml) was added sulfamic acid (63.7 mg, 0.66 mmol) and 2-methyl-1-butene (0.04 ml, 0.39 mmol). The solution was cooled to 0° C. and sodium chlorite (52.4 mg, 0.58 mmol) in water (2 ml) was added dropwise. After 60 minutes the mixture was quenched with saturated aqueous sodium thiosulfate solution (20 ml) and extracted with ethyl acetate (3×10 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give the title compound as oil. 71 mg.

Workup

customAfter 60 minutes the mixture was quenched with saturated aqueous sodium thiosulfate solution (20 ml)
extractionextracted with ethyl acetate (3×10 ml)
dry with materialThe organic layer was dried (MgSO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-8f7f82c4cc2c425ba7bccaa303d35dd6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365551B2

Reaction notes

Loading…