3-Hydroxyacetanilide → HCID 22857709, compound

HRID 2259203Notes

Reaction equation

HRID 2259203 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([NH:18][C:19]1[CH:20]=[C:21](O)[CH:22]=[CH:23][CH:24]=1)(=[O:17])[CH3:16]>C1COCC1>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:18][C:15](=[O:17])[CH3:16])[CH:24]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 121243-HydroxyacetanilideHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 22857709HCID 22857709, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.5 g (7.46 mmol) sample of (S)-1-BOC-2-pyrrolidinemethanol (from Aldrich) and 1.69 g (11.19 mmol) of 3-acetamidophenol (Aldrich) were added to a complex of TPP and TBAD, (prepared as in Example 5b above, 11.19 mmol of each) in 50 mL of THF. The reaction was stirred for 16 hr, the solvents were removed under vacuum, and the residue was chromatographed on silica gel, eluting with 100:3 chloroform:methanol to give 1.62 g of the title compound.

Workup

  1. customthe solvents were removed under vacuum
  2. customthe residue was chromatographed on silica gel
  3. washeluting with 100:3 chloroform

Sources & evidence

ORD record
ord-15e2c672925a499a82328b46ab93a989
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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