Lithium Hydroxide → HCID 67394149, compound

HRID 909262Notes

Reaction equation

HRID 909262 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[Li+].[OH-].[NH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC>CO.CN(C=O)C.O.C1COCC1>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([S:18]([NH:17][CH:14]2[CH2:13][CH2:12][CH:11]([C:9]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[O:8])[CH2:16][CH2:15]2)(=[O:19])=[O:20])=[CH:26][CH:25]=1)#[N:28]

Participants

10

Reactant 5

HCID 3939Lithium HydroxideHCID 4837PiperazineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178510111HCID 178510111, compound

Product 1

HCID 67394149HCID 67394149, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.9 g (4.7 mmol) trans-4-(4-cyano-benzenesulfonylamino)-cyclohexanecarboxylic acid benzyl ester and 0.8 g (1.9 mmol) LiOH in a mixture of methanol, THF and water was stirred at room temperature for 2 h. The mixture was evaporated to dryness and 10 mL DMF, 0.7 g (8.1 mmol) piperazine, 2.87 g (8.9 mmol) TBTU and 2.26 g (22 mmol) NEt3 was added. The mixture was stirred at room temperature for 1 h and evaporated to dryness. The residue was purified by column chromatography on silica obtaining 0.3 g (16%) of the title compound. MS (m/e): 377.1 (MH+).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. customevaporated to dryness
  4. customThe residue was purified by column chromatography on silica obtaining 0.3 g (16%) of the title compound

Sources & evidence

ORD record
ord-ce6f1bdc60ab471a994d334a70443cf8
Source dataset
uspto-grants-2011_09
Patent number
US08017773B2

Reaction notes

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