Tetrahydrofuran → HCID 57889921, compound

HRID 1016143Notes

Reaction equation

HRID 1016143 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:33])[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C@H:15]([NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]([O:27]CC)=[O:26])[N:24]=3)[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:32])[CH3:31])=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:33])[CH2:13][CH2:12][N:11]([C:14](=[O:30])[C@H:15]([NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[N:24]=3)[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:31])[CH3:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57889844HCID 57889844, compound

Product 1

HCID 57889921HCID 57889921, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylamino)thiazole-4-carboxylate (69 mg, 0.140 mmol) in MeOH (0.28 ml)/THF (0.280 ml) was added NaOH, IN (0.140 ml, 0.140 mmol) and the reaction stirred at room temperature. The reaction was stirred for 8 h and then neutralized with 1 N HCL. The solvents were removed and water (˜1 mL) was added. The resulting solids were stirred and sonicated briefly, filtered and rinsed with water. HPLC purity of crude solids, ˜90%; MS found: 466.26 (M+)+.

Workup

  1. stirringThe reaction was stirred for 8 h
  2. customThe solvents were removed
  3. additionwater (˜1 mL) was added
  4. stirringThe resulting solids were stirred
  5. customsonicated briefly
  6. filtrationfiltered
  7. washrinsed with water

Sources & evidence

ORD record
ord-d559a75357954c69b7f71b3f3ca7a473
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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