Acetic Acid → HCID 86695190, compound

HRID 1504032Notes

Reaction equation

HRID 1504032 reaction equation
[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2)(=[O:4])=[O:3].[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][C:28]1=[O:33].C(O)(=O)C.[Na]BCC(O)=O.C(OOC(=O)C)(=O)C>CO>[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][CH:23]([N:30]5[CH2:31][CH2:32][NH:27][C:28](=[O:33])[CH2:29]5)[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 231360Piperazin-2-oneHCID 86695188HCID 86695188, compoundHCID 178476735HCID 178476735, compound

Product 1

HCID 86695190HCID 86695190, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(3S)-12-[(4-oxocyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]methyl methanesulfonate (500 mg, 1.26 mmol, 1.00 equiv) in methanol (10 mL) was added piperazin-2-one (126 mg, 1.26 mmol, 1.00 equiv) and acetic acid (1 mL). The solution was stirred for 1 h and then acetyl ethaneperoxoate sodioboranyl acetate (534 mg, 2.52 mmol, 2.00 equiv) was added. Stirring was continued for 2 h at 0° C. The mixture was then quenched with saturated aqueous sodium bicarbonate, extracted with DCM (60 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The desired [(3S)-12-[[4-(3-oxopiperazin-1-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]methyl methanesulfonate (450 mg, 74%) was obtained as a yellow solid.

Workup

  1. stirringStirring
  2. waitwas continued for 2 h at 0° C
  3. customThe mixture was then quenched with saturated aqueous sodium bicarbonate
  4. extractionextracted with DCM (60 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3c6ac703f9d940999f89e76c248fdb05
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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