Triphenylphosphine → 4-isopropyl-6-[3-(phenylmethyloxycarbonyl)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289875Notes

Reaction equation

HRID 1289875 reaction equation
[CH:1]([C:4]1[C:9]2[C:10](=[O:33])[N:11]([CH2:15][O:16][C:17]3[N:21]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[N:20]=[C:19]([C:29]([F:32])([F:31])[F:30])[CH:18]=3)[S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([OH:34])[CH:5]=1)([CH3:3])[CH3:2].[C:35]1([CH2:41][O:42][C:43](=[O:48])[CH2:44][CH2:45][CH2:46]O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCOC(/N=N/C(OCC)=O)=O.P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[CH:1]([C:4]1[C:9]2[C:10](=[O:33])[N:11]([CH2:15][O:16][C:17]3[N:21]([C:22]4[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=4)[N:20]=[C:19]([C:29]([F:30])([F:31])[F:32])[CH:18]=3)[S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([O:34][CH2:46][CH2:45][CH2:44][C:43]([O:42][CH2:41][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:48])[CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14443958Benzyl 4-hydroxybutanoateHCID 189225854-isopropyl-6-hydroxy-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 189225544-isopropyl-6-[3-(phenylmethyloxycarbonyl)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 34.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-isopropyl-6-hydroxy-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (9.95 g; 19.3 mmol), 4-hydroxybutanoic acid phenylmethyl ester (4.49 g;23.16 mmol), DEAD (4.03 g; 23.16 mmol) was dissolved in 193 ml of THF at 0° C. and then (Ph)3P (6.068 g; 23.16 mmol) was added at 0° C. The above mixture was stirred overnight at room temperature, concentrated in vacuo, and the residue was purified by column chromatography (2×, silica gel; 12-50% ethyl acetate/hexane; methylene chloride/hexane, 1/4-30/1) to afford 4.55 g (34%) of 4-isopropyl-6-[3-(phenylmethyloxycarbonyl)propoxy]-2-[1-(4-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =4-Cl--Ph; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-O(CH2)3CO2 CH2Ph) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by column chromatography (2×, silica gel; 12-50% ethyl acetate/hexane; methylene chloride/hexane, 1/4-30/1)

Sources & evidence

ORD record
ord-a8a285895aeb4d499edd97d5668783db
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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