Water → HCID 136386389, compound

HRID 323654Notes

Reaction equation

HRID 323654 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([Cl:21])=[C:19]([CH2:22][N:23]3[C:27](=[O:28])[CH2:26][CH2:25][C:24]3=[O:29])[N:18]=[C:17]3[S:30][C:31]4[CH2:32][NH:33][CH2:34][CH2:35][C:36]=4[C:16]=23)=[CH:11][CH:10]=1)C1C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:21][C:20]1[C:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[C:16]2[C:36]3[CH2:35][CH2:34][NH:33][CH2:32][C:31]=3[S:30][C:17]2=[N:18][C:19]=1[CH2:22][N:23]1[C:24](=[O:29])[CH2:25][CH2:26][C:27]1=[O:28]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15523764HCID 15523764, compound

Product 1

HCID 136386389HCID 136386389, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Example 14 (600 mg) in methylene chloride (20 ml) was added titanium tetrachloride (1.1 g) while cooling with ice. After stirring for 2 hours at room temperature followed by addition of water (10 ml), the stirring was continued for further 15 minutes. After discontinuing the stirring, the aqueous layer was isolated, and neutralized with saturated aqueous sodium bicarbonate, and then extracted with ethyl acetate-tetrahydrofurane (3:1, v/v). The extracted organic layer was washed with water, dried (MgSO4) and then the solvent was distilled off to obtain the title compound (305 mg, 62%). The product was recrystallized from dimethylformamide-water. A colorless prism crystal. M.p. 286 to 287° C.

Workup

  1. temperaturewhile cooling with ice
  2. waitthe stirring was continued for further 15 minutes
  3. customthe aqueous layer was isolated
  4. extractionextracted with ethyl acetate-tetrahydrofurane (3:1
  5. washThe extracted organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0f4d92d833b54f6ab53a3fb74e75242b
Source dataset
uspto-grants-2001_04
Patent number
US06214838B1

Reaction notes

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