3-(Phenylsulfonyl)propanoic acid → Diisopropylcarbodiimide

HRID 413031Notes

Reaction equation

HRID 413031 reaction equation
C1(S(CCC(O)=O)(=O)=O)C=CC=CC=1.O[C:16]1[C:24]2[N:23]=NN[C:20]=2C=CC=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)[N:33]2[CH2:36][CH:35]([NH:37]C(=O)C3C=CC(S(C)(=O)=O)=CC=3)[CH2:34]2)=[CH:28][CH:27]=1>CN(C)C=O.ClCCl>[CH:32]([N:33]=[C:34]=[N:23][CH:24]([CH3:20])[CH3:16])([CH3:50])[CH3:29].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)[N:33]2[CH2:34][CH:35]([NH2:37])[CH2:36]2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 5552523-(Phenylsulfonyl)propanoic acidHCID 17751339HCID 17751339, compoundHCID 178418300HCID 178418300, compound

Product 2

HCID 12734DiisopropylcarbodiimideHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

By carrying out the operation according to the procedure of Example 31, starting with 58.5 mg of 3-phenylsulfonylpropionic acid, 26.4 mg of hydroxybenzotriazole in solution in 0.5 cm3 of dimethylformamide, 0.0302 cm3 of diisopropylcarbodiimide, a solution of 30 mg of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 0.5 cm3 of anhydrous dichloromethane, and 3 cm3 of anhydrous dichloromethane, N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-4-methanesulfonylbenzamide is obtained in the form of a lacquer [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.71 (t, J=7.5 Hz: 2H) 2.86 (mt: 2H); from 3.40 to 3.55 (mt: 4H); 4.26 (s: 1H); 4.45 (mt: 1H); 6.22 (broad d, J=7.5 Hz: 1H); from 7.20 to 7.35 (mt: 8H); 7.59 (broad t, J=7.5 Hz: 2H); 7.69 (tt, J=7.5 and 1.5 Hz: 1H); 7.93 (broad d, J=7.5 Hz: 2H)].

Sources & evidence

ORD record
ord-b2dbd4a2ba954123a532088c9a4bb0d2
Source dataset
uspto-grants-2003_05
Patent number
US06566356B2

Reaction notes

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