Hydrochloric Acid → HCID 86598220, compound

HRID 501775Notes

Reaction equation

HRID 501775 reaction equation
[CH:1]1([O:6][C:7]2[CH:37]=[CH:36][C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:24][CH2:25][C:26]4[CH:35]=[CH:34][C:29]5[C:30]([OH:33])=[N:31][O:32][C:28]=5[CH:27]=4)=[C:17]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:18]=3)=[O:12])=[C:9]([OH:38])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:46](Cl)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.Cl>C(Cl)Cl.O>[CH:1]1([O:6][C:7]2[CH:37]=[CH:36][C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:24][CH2:25][C:26]4[CH:35]=[CH:34][C:29]5[C:30](=[O:33])[N:31]([C:46]([C:47]6[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=6)([C:59]6[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=6)[C:53]6[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=6)[O:32][C:28]=5[CH:27]=4)=[C:17]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:18]=3)=[O:12])=[C:9]([OH:38])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178525321HCID 178525321, compound

Product 1

HCID 86598220HCID 86598220, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5.80 g of 3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl} propanoic acid was suspended in 58 mL of methylene chloride, to which 6.2 mL of triethylamine was added at room temperature followed by addition of 3.44 g of trityl chloride in an ice bath, and this mixture was stirred for 30 minutes at room temperature. The reaction mixture to which water was added was adjusted to pH 3 with 6M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water, the solvent was distilled out under reduced pressure. The resultant residue was washed with hexane and then purified by silica gel column chromatography [eluent; chloroform:ethanol=50:1] to yield 6.83 g of 3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-oxo-2-trityl-2,3-dihydro-1,2-benzisoxazol-6-yl)methoxy]phenyl} propanoic acid as yellow solid.

Workup

  1. additionwas added at room temperature
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. distillationthe solvent was distilled out under reduced pressure
  5. washThe resultant residue was washed with hexane
  6. custompurified by silica gel column chromatography [eluent; chloroform:ethanol=50:1]

Sources & evidence

ORD record
ord-9ad2685f57b84a94991bf232e76449b6
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

Loading…