Water → HCID 131728682, compound

HRID 1363390Notes

Reaction equation

HRID 1363390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][NH:26][CH2:25][C@H:24]1[OH:29].[CH3:30][CH2:31][CH2:32]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26]([CH2:30][CH2:31][CH3:32])[CH2:25][C@H:24]1[OH:29]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 131728681HCID 131728681, compound

Product 1

HCID 131728682HCID 131728682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of compound of example 128 (0.871 g, 2.09 mmol), n-propyl bromide (0.335 g, 2.72 mmol) and anhydrous K2CO3 (1.15 g, 8.33 mmol) in dry DMF (20 mL) was stirred at 25° C. for 2 h. The reaction mixture was treated with water and extracted with EtOAc (2×100 mL). The organic extract was washed with water, dried (anhydrous Na2SO4) and concentrated. The crude obtained was purified on a silica gel column using a mixture of 1% MeOH+1% liquor NH3 in CHCl3 as eluant to get the title compound.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. customThe crude obtained
  7. customwas purified on a silica gel column
  8. additiona mixture of 1% MeOH+1% liquor NH3 in CHCl3 as eluant

Sources & evidence

ORD record
ord-ea02f1108afc4dc7b2086293897d6b25
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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