Potassium Hydroxide → HCID 59737304, compound

HRID 1907753Notes

Reaction equation

HRID 1907753 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]4[CH:25]=[C:24]([C:26]5[S:27][CH:28]=[CH:29][CH:30]=5)[CH:23]=[CH:22][C:21]=4[NH:31]C(=O)OC(C)(C)C)=[O:18])[CH2:13][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(Cl)Cl.FC(F)(F)C(O)=O.[OH-].[K+]>C(Cl)Cl.[Cl-].[Na+].O>[NH2:31][C:21]1[CH:22]=[CH:23][C:24]([C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)=[CH:25][C:20]=1[NH:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)[CH2:12][CH2:13]1)=[O:18]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 59737378HCID 59737378, compound

Product 1

HCID 59737304HCID 59737304, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of compound 315 (165 mg, 0.31 mmol) in a mixture DCM-trifluoroacetic acid (3 mL, 2:1 ratio) was stirred at room temperature for 1.5 h; diluted with DCM and washed with a solution of KOH (830 mg, 15 mmol) in brine (15 mL), then brine, dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (elution with 5% to 10% MeOH in DCM) gave title compound 316 (87 mg, 0.20 mmol, 64% yield) as a pale yellow solid.

Workup

  1. dry with materialbrine, dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification
  5. washby flash column chromatography (elution with 5% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-ab8e5515343d4783bc0f3c6d975b3d09
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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