HCID 54318654, compound → HCID 19611331, compound

HRID 1602500Notes

Reaction equation

HRID 1602500 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:44]=[C:45]([NH:47]C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH:46]=2)[C:15]([NH:17][C:18]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:28]=[CH:27][C:19]=2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:16])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.O1CCCC1.[C].[Pd]>[NH2:47][C:45]1[CH:44]=[C:14]([CH:13]=[C:12]([O:11][CH2:10][C:7]2[S:8][CH:9]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[N:6]=2)[CH:46]=1)[C:15]([NH:17][C:18]1[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)(=[O:35])=[O:36])[CH:28]=[CH:27][C:19]=1[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:16]

Participants

6

Reactant 2

HCID 54318654HCID 54318654, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19611331HCID 19611331, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[3-[(4-tert-butyl-2-thiazolyl)methoxy]-5-(4-nitrobenzyloxycarbonylamino)benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (0.50 g, 0.57 mmol) was dissolved in a mixed solution of ethanol (10 ml) and tetrahydrofuran (10 ml), 10% palladium-carbon (0.10 g) was added to the solution, and the mixture was stirred at room temperature for 3 hours in an atmosphere of hydrogen. The reaction solution was filtered and the resulting filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent=acetone:chloroform=3:100) and crystallized from acetonitrile to give ethyl 2-[3-amino-5-[(4-tert-butyl-2-thiazolyl)methoxy]benzoylamino]-4-[3-(4- chlorophenylsulfonyl)propyl]phenoxyacetate (0.17 g, 0.24 mmol, 43%) as light yellow crystals. Its structure is shown in Table 30.

Workup

  1. additionwas added to the solution
  2. filtrationThe reaction solution was filtered
  3. concentrationthe resulting filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent=acetone:chloroform=3:100)
  5. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-c6a393af506b474cac88e0d4bc9e4c0a
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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