Water → HCID 22401680, compound

HRID 260515Notes

Reaction equation

[NH:1]1[C:5]2[N:6]=[C:7]3[S:13][CH2:12][CH2:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=[N:2]1.[H-].[Na+].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].O>CN(C)C=O>[C:21]([O:20][C:18]([CH2:17][N:1]1[C:5]2[N:6]=[C:7]3[S:13][CH2:12][CH2:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=[N:2]1)=[O:19])([CH3:24])([CH3:23])[CH3:22].[C:21]([O:20][C:18]([CH2:17][N:2]1[CH:3]=[C:4]2[C:5]([N:6]=[C:7]3[S:13][CH2:12][CH2:11][N:8]3[C:9]2=[O:10])=[N:1]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

In 120 ml of dimethylformamide was dissolved 3.00 g (15.4 mmol) of Compound 1 prepared in Example 1, and 1.86 g (46.3 mmol) of sodium hydride (60%) and 7.48 ml (46.3 mmol) of tert-butyl bromoacetate were added to the solution, followed by stirring at 50° C. for 12 hours. After addition of water and evaporation of the solvent, the residue was subjected to partition between chloroform and water, and the chloroform layer was concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (100:1). The first and second main fractions gave 1.59 g (33%) of Compound 34 and 0.97 g (20%) of Compound 35, respectively. Each compound was recrystallized from ethanol for purification.

Workup

additionwere added to the solution
customto partition between chloroform and water
concentrationthe chloroform layer was concentrated to dryness under reduced pressure
washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record: ord-f121fdd50acd4477bf26853fbcc73423
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05527908

Reaction notes

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