Sodium Hydroxide → HCID 67454510, compound

HRID 227709Notes

Reaction equation

HRID 227709 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]([C:14]([O:16]C)=O)=[C:12]([CH2:18][NH:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][N:24]=[CH:23]4)[NH:11][C:10](=[O:29])[NH:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].N=C=N>CO.O.CCOC(C)=O.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:9][C:10](=[O:29])[NH:11][CH:12]3[CH2:18][N:19]([C:20]4[CH:21]=[C:22]5[C:26](=[CH:27][CH:28]=4)[NH:25][N:24]=[CH:23]5)[C:14](=[O:16])[CH:13]23)=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 160435CarbodiimideHCID 67454970HCID 67454970, compound

Product 1

HCID 67454510HCID 67454510, compoundYield 11%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The product of step (b) (132 mg, 0.334 mmol, 1.00 equiv) and NaOH (2.5 N, 0.5 mL) were dissolved in methanol (2 mL) and heated to 60° C. in a sealed tube for three hours. The reaction mixture was diluted with water (˜50 mL) and EtOAc (˜50 mL), stirred, and separated. The aqueous layer was adjusted to pH 1 with 2N HCl and extracted with EtOAc. The organic layer was concentrated en vacuo and the residue (39 mg, 0.102 mmol, 1 equiv) was dissolved in DMF (5 mL). PS-carbodiimide resin (140 mg, 0.153 mmol, 1.5 equiv) was added and the reaction was stirred at room temperature for 18 hours. The reaction mixture was filtered and washed twice alternately with methanol and methylene chloride. The filtrate was concentrated en vacuo and the residue was purified by silica gel column (0-10% MeOH in CH2Cl2). The residue was triturated with CH2Cl2/Hexane to give 4 mg of the title compound as a beige powder (11%). MS (ES+) m/e 364 [M+H]+

Workup

  1. customseparated
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated en vacuo
  4. stirringthe reaction was stirred at room temperature for 18 hours
  5. filtrationThe reaction mixture was filtered
  6. washwashed twice alternately with methanol and methylene chloride
  7. concentrationThe filtrate was concentrated en vacuo
  8. customthe residue was purified by silica gel column (0-10% MeOH in CH2Cl2)
  9. customThe residue was triturated with CH2Cl2/Hexane

Sources & evidence

ORD record
ord-660667868e6a4006be09282babf0c273
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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