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

HRID 1818800Notes

Reaction equation

HRID 1818800 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][S:9]1(=[O:18])=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:39][CH2:40][CH:41]([N:48]([CH3:56])[C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:39][CH2:40][CH:41]([N:48]([CH3:56])[C:49](=[O:55])[O:50][C:51]([CH3:53])([CH3:52])[CH3:54])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[S:9]1(=[O:18])=[O:17]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 468330941-(2-Fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideHCID 71967731Tert-butyl (3-hydroxy-1-phenylpropyl)methylcarbamate

Product 1

HCID 86621286tert-butyl {3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-phenylpropyl}methylcarbamate

Procedure

In an analogous manner to general procedure II, 1-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared in an analogous manner as described in general procedure I, 108 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 0.13 g tert-butyl {3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-phenylpropyl}methylcarbamate.

Sources & evidence

ORD record
ord-5bc9c5b54b75406494c8566bc8188156
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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