Hydrochloric Acid → HCID 57687366, compound

HRID 559068Notes

Reaction equation

HRID 559068 reaction equation
[Li+].[OH-].C(OC([C:8]1[C:13]([Cl:14])=[CH:12][C:11](=[O:15])[N:10]([CH3:16])[C:9]=1[NH:17][CH3:18])=O)C.Cl>CO.C1COCC1>[Cl:14][C:13]1[CH:8]=[C:9]([NH:17][CH3:18])[N:10]([CH3:16])[C:11](=[O:15])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57687362HCID 57687362, compound

Product 1

HCID 57687366HCID 57687366, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

An aqueous solution of LiOH (2N, 400 mmol, 200 mL) was slowly added at 0° C. to a stirring solution of example 31c (16.0 g, 65.6 mmol) in MeOH/THF (200 mL/100 mL). The reaction mixture was allowed to warm to room temperature and stirred for 43 h. The solution was adjusted to neutral pH with 1N HCl and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to give 6.8 g (60%) of clean desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.87 (q, 1H, J=4.4 Hz), 5.63 (s, 1H), 5.35 (s, 1H), 3.25 (s, 3H), 2.72 (d, 3H, J=4.4 Hz). MS (ES) [m+H] calc'd for C7H9ClN2O, 173, 175; found 173, 175.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9496ecd828a349e5aa40e636982a0865
Source dataset
uspto-grants-2011_11
Patent number
US08063066B2

Reaction notes

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