Diisopropylethylamine → trans-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid [cyano-(3-hydroxy-phenyl)-methyl]-amide

HRID 990914Notes

Reaction equation

HRID 990914 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([OH:20])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.F[B-](F)(F)F.C[N+](C)=C(N(C)C)O.C(N(C(C)C)C(C)C)C.[NH2:43][CH:44]([C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([OH:53])[CH:48]=1)[C:45]#[N:46]>CC#N>[C:45]([CH:44]([NH:43][C:18]([C@@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C@H:12]1[NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])=[O:20])[C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([OH:53])[CH:48]=1)#[N:46]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 13074157Tetramethyluronium tetrafluoroborateHCID 16793683Amino-(3-hydroxy-phenyl)-acetonitrileHCID 69656371Trans-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid

Product 1

HCID 10182237trans-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid [cyano-(3-hydroxy-phenyl)-methyl]-amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Trans-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid (0.095 g, 0.3 mmol) is dissolved in CH3CN. O-1,2-Dihydro-2-oxo-1-pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TPTU, 90.2 mg, 0.3 mmol), N-Ethyldiisopropylamine (DIPEA, 0.208 ml, 1.21 mmol) are added. The amino-(3-hydroxy-phenyl)-acetonitrile in CH3CN (1.5 ml) is added. The mixture is stirred at RT for 16 hours. The solution is filtered and concentrated. The residue is dissolved in CH2Cl2 (15 mL) and extracted with NH4Cl (2×10 ml). The H2O layers are extracted with CH2Cl2 (2×15 ml). The collected CH2Cl2 layers are dried over MgSO4 and evaporated. The solid is purified by preparative HPLC.

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in CH2Cl2 (15 mL)
  4. extractionextracted with NH4Cl (2×10 ml)
  5. extractionThe H2O layers are extracted with CH2Cl2 (2×15 ml)
  6. dry with materialThe collected CH2Cl2 layers are dried over MgSO4
  7. customevaporated
  8. customThe solid is purified by preparative HPLC

Sources & evidence

ORD record
ord-caf89cdf3d194145a88fa364620632ac
Source dataset
uspto-grants-2002_10
Patent number
US06462076B2

Reaction notes

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