Sulfamic Acid → HCID 66610949, compound

HRID 2204723Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([CH:25]=[O:26])[C:22]([Cl:27])=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(CC)=C.S(=O)(=O)([OH:35])N.Cl([O-])=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.CS(C)=O.O>[CH2:1]([O:8][C:9]1[C:10]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:21][C:22]([Cl:27])=[C:23]([CH:24]=1)[C:25]([OH:35])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of benzyl 2-(benzyloxy)-5-chloro-4-formylbenzoate (may be prepared as described in D73) (1.4 g, 3.68 mmol) in tetrahydrofuran (THF) (8 mL) and dimethyl sulfoxide (DMSO) (0.8 mL) were added 2-methyl-1-butene (0.792 mL, 7.35 mmol) and sulfamic acid (1.214 g, 12.50 mmol). The solution was cooled to 0° C. and a solution of sodium chlorite (0.997 g, 11.03 mmol) in water (8 mL) was added. The mixture was stirred for one hour, then saturated sodium thiosulfate solution was added (15 mL) and the mixture was stirred for another 10 minutes. The mixture was extracted with EtOAc (3×20 mL). The organic layer was washed with water (10 mL) and 2M HCl (10 mL), dried over MgSO4 and concentrated in vacuo to give the title product as an off-white solid (1.46 g, 100% yield).

Workup

stirringthe mixture was stirred for another 10 minutes
extractionThe mixture was extracted with EtOAc (3×20 mL)
washThe organic layer was washed with water (10 mL) and 2M HCl (10 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1c12dba9505540f4a0cd59691835e98a
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365551B2

Reaction notes

Loading…