Diisopropylcarbodiimide → HCID 15521570, compound

HRID 413028Notes

Reaction equation

HRID 413028 reaction equation
C(N=C=NC(C)C)(C)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:18]2[CH2:21][CH:20]([NH2:22])[CH2:19]2)=[CH:13][CH:12]=1.[C:30]1([S:36]([CH2:39][C:40](O)=[O:41])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.OC1C2N=NNC=2C=CC=1>ClCCl.CN(C)C=O.CO>[C:30]1([S:36]([CH2:39][C:40]([NH:22][CH:20]2[CH2:19][N:18]([CH:17]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[C:14]3[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=3)[CH2:21]2)=[O:41])(=[O:37])=[O:38])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

8

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 59543(phenylsulfonyl)acetic acidHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamineHCID 178418300HCID 178418300, compound

Product 1

HCID 15521570HCID 15521570, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.031 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 are added to a solution of 80.1 mg of benzenesulfonylacetic acid, 27 mg of hydroxybenzotriazole in solution in 0.5 cm3 of dimethylformamide under an inert argon atmosphere, at a temperature in the region of 23° C. After 17 hours at a temperature in the region of 23° C., the reaction mixture is loaded onto a 3-cm3 SPE cartridge containing 1 g of SCX phase preconditioned with methanol. After washing with twice 5 cm3 of methanol and then 4 cm3 of 0.1 N ammoniacal methanol, the expected product is eluted with 4 cm3 of 1 N ammoniacal methanol. The fraction containing the expected product is evaporated under an air stream at a temperature in the region of 45° C. and then dried under reduced pressure (1 mbar) at a temperature in the region of 40° C. 2-Benzenesulfonyl-N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}acetamide is thus obtained in the form of a white solid [1H NMR spectrum (500 MHz, CDCl3, δ in ppm): 2.96 (mt: 2H) 3.51 (mt: 2H); 4.00 (s: 2H); 4.34 (unresolved complex: 1H); 4.48 (mt: 1H); 7.10 (unresolved complex: 1H); from 7.20 to 7.45 (mt: 8H); 7.57 (t, J=8 Hz: 2H); 7.70 (t, J=8 Hz: 1H); 7.90 (d, J=8 Hz: 2H)].

Workup

  1. additioncontaining 1 g of SCX phase
  2. washAfter washing with twice 5 cm3 of methanol
  3. wash4 cm3 of 0.1 N ammoniacal methanol, the expected product is eluted with 4 cm3 of 1 N ammoniacal methanol
  4. additionThe fraction containing the expected product
  5. customis evaporated under an air stream at a temperature in the region of 45° C.
  6. customdried under reduced pressure (1 mbar) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-01f213fe10bb46579e32ca8eaf154302
Source dataset
uspto-grants-2003_05
Patent number
US06566356B2

Reaction notes

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