Triphenylphosphine → tert-butyl {3-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-phenylpropyl}methylcarbamate

HRID 1818798Notes

Reaction equation

HRID 1818798 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][S:10]1(=[O:19])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:40][CH2:41][CH:42]([N:49]([CH3:57])[C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:40][CH2:41][CH:42]([N:49]([CH3:57])[C:50](=[O:56])[O:51][C:52]([CH3:54])([CH3:53])[CH3:55])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:10]1(=[O:18])=[O:19]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 687119791-(2,3-Difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideHCID 71967731Tert-butyl (3-hydroxy-1-phenylpropyl)methylcarbamate

Product 1

HCID 86621285tert-butyl {3-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-phenylpropyl}methylcarbamate

Procedure

In an analogous manner to general procedure II, 1-(2,3-difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared in an analogous manner as described in general procedure I, 115 mg, 0.41 mmol) was treated with triphenylphosphine (0.13 g, 0.49 mmol), tert-butyl (3-hydroxy-1-phenylpropyl)methylcarbamate (0.12 g, 0.45 mmol), and diisopropylazodicarboxylate (0.095 mL, 0.49 mmol) to provide 0.12 g tert-butyl {3-[3-(2,3-difluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-phenylpropyl}methylcarbamate.

Sources & evidence

ORD record
ord-54302b63edfc4e02a350329d02d43361
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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