Triphenylphosphine → tert-butyl 2-[(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)methyl]morpholine-4-carboxylate

HRID 1818775Notes

Reaction equation

[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][S:8]2(=[O:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH2:19][CH:20]1[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O-])=O)=NC([O-])=O>O1CCCC1>[O:17]=[S:8]1(=[O:16])[N:9]([CH2:19][CH:20]2[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:21]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared analogously as in general procedure I, 246 mg, 1.00 mmol), tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (228 mg, 1.05 mmol, 1.05 equiv.) and triphenylphosphine (289 mg, 1.10 mmol, 1.1 equiv.) in tetrahydrofuran (5 mL) was cooled to 0° C. in an ice bath. Diispropyl azodicarboxylate (0.22 mL, 1.1 mmol, 1.1 equiv.) was added dropwise via a syringe. The reaction mixture was stirred overnight while warming to room temperature. Solvent was removed under reduced pressure and the residue was purified by Isco flash column chromatography (silica gel, 3-30% ethyl acetate/hexane) to give 398 mg (89%) of tert-butyl 2-[(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)methyl]morpholine-4-carboxylate as a white foam. MS (ESI) m/z 445.9 ([M+H]+).

Workup

temperaturewhile warming to room temperature
customSolvent was removed under reduced pressure
customthe residue was purified by Isco flash column chromatography (silica gel, 3-30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-530ea955cd3b4107975f9a86abe8b4ea
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601722B2

Reaction notes

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