Hydrochloric Acid → HCID 86753007, compound

HRID 482015Notes

Reaction equation

HRID 482015 reaction equation
[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:49][CH2:50][C:51]([OH:53])=[O:52].C(N(CC)CC)C.Cl>C(#N)C.O>[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].[NH2:49][CH2:50][C:51]([OH:53])=[O:52]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 750GlycineHCID 3715IndomethacinHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 86753007HCID 86753007, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a suspension of indomethacin (500 mg, 1.40 mmole) in acetonitrile (20 ml), HOSu (177 mg, 1.54 mmole) and DCC (317 mg, 1.54 mmole) were added and the solution stirred at room temperature for 2 h. A solution of glycine (178 mg, 2.38 mmole) and triethylamine (184 mg, 1.82 mmole) in water (10 ml) was added to the resulting indomethacin hydroxysuccinimide ester and stirred for 2 h, diluted with water (60 ml), acidified with 1M HCl and extracted with ethyl acetate (80 ml). After drying (MgSO4) the solution was evaporated to dryness to give a yellow solid, which was recrystallised from ethylacetate/hexane to give the title product (406 mg, 70% theory) in 95% purity as determined by 1H NMR.

Workup

  1. additionwere added
  2. stirringstirred for 2 h
  3. extractionextracted with ethyl acetate (80 ml)
  4. dry with materialAfter drying (MgSO4) the solution
  5. customwas evaporated to dryness
  6. customto give a yellow solid, which
  7. customwas recrystallised from ethylacetate/hexane

Sources & evidence

ORD record
ord-a17b6f988ea94ea6a100e6c594912112
Source dataset
uspto-grants-1998_08
Patent number
US05792786

Reaction notes

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