Sodium Hydroxide → 6-chloro-2-(4-hydroxymethyl-2-furoyl)-3-[[(S)-2-hydroxypropionyl]amino]indole

HRID 379894Notes

Reaction equation

HRID 379894 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:11]([C:13]2[N:14](C(OCC)=O)[C:15]3[C:20]([C:21]=2[NH:22][C:23](=[O:30])[C@@H:24]([O:26]C(=O)C)[CH3:25])=[CH:19][CH:18]=[C:17]([Cl:31])[CH:16]=3)=[O:12])[O:9][CH:10]=1)(=O)C.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:31][C:17]1[CH:16]=[C:15]2[C:20]([C:21]([NH:22][C:23](=[O:30])[C@@H:24]([OH:26])[CH3:25])=[C:13]([C:11]([C:8]3[O:9][CH:10]=[C:6]([CH2:5][OH:4])[CH:7]=3)=[O:12])[NH:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 540822552-(4-Acetoxymethyl-2-furoyl)-6-chloro-1-ethoxycarbonyl-3-[[(S)-2-acetoxypropionyl]amino]indole

Product 1

HCID 544965056-chloro-2-(4-hydroxymethyl-2-furoyl)-3-[[(S)-2-hydroxypropionyl]amino]indoleYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(4-acetoxymethyl-2-furoyl)-6-chloro-1-ethoxycarbonyl-3-[(S)-2-acetoxypropionylamino]indole (step 1, 267 mg, 0.494 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (2 ml). After stirrig for 3 h, the mixture was poured into saturated aqueous ammonium chloride (20 ml) and extracted with ethyl acetate (80 ml). The organic layer was washed with brine (20 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with dichloromethane/methanol (50/1) and recrystallized from 2-propanol/isopropyl ether to give 43 mg (24%) of the titled compound as yellow solids. m.p.: 213-214° C. 1H-NMR (CDCl3) δ: 11.4 (1H, br s), 10.8 (1H, br s), 8.35 (1H, d, J=8.90 Hz), 7.76 (1H, s), 7.53 (1H, d, J=1.81 Hz), 7.45 (1H, s), 7.01 (1H, dd, J=8.90 Hz, 1.81 Hz), 4.58 (2H, d, J=5.11 Hz), 4.36 (1H, q, J=6.92 Hz), 1.52 (3H, d, J=6.92 Hz).

Workup

  1. extractionextracted with ethyl acetate (80 ml)
  2. washThe organic layer was washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography
  6. washeluting with dichloromethane/methanol (50/1)
  7. customrecrystallized from 2-propanol/isopropyl ether

Sources & evidence

ORD record
ord-bfb3559eb501496da2af80c06d41cacf
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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