Water → HCID 178523766, compound

HRID 2391014Notes

Reaction equation

HRID 2391014 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.O.C(N(CC)CC)C.[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:20]=1[C:21](Cl)=[O:22]>C1COCC1>[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][C:20]=1[C:21]([NH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([CH2:8][OH:9])[CH2:4][CH2:3]1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27781062-Chloro-5-(trifluoromethyl)benzoyl chlorideHCID 178511559HCID 178511559, compound

Product 1

HCID 178523766HCID 178523766, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cis-(4-Amino-cyclohexyl)-methanol (Tetrahedron Lett., 1970, 11, 4285-4288) (0.75 g, 5.80 mmol) in THF (10 ml) is added water (1.8 mL), triethylamine (2.023 mL, 14.51 mmol) and 2-chloro-5-(trifluoromethyl)benzoyl chloride (1.411 g, 5.80 mmol). The RM is stirred at RT for 1 hour. The reaction mixture is partitioned between EtOAc and water. The organic phase is washed successively with water, saturated sodium bicarbarbonate and saturated brine, dried over MgSO4, filtered and the solvent removed in vacuo. Purification by chromatography on a pre-packed silica gel column using 0-100% EtOAc in isohexane gradient elution gave the desired product as a colourless solid.

Workup

  1. customThe reaction mixture is partitioned between EtOAc and water
  2. washThe organic phase is washed successively with water, saturated sodium bicarbarbonate and saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customPurification by chromatography on a pre-packed silica gel column
  7. wash0-100% EtOAc in isohexane gradient elution

Sources & evidence

ORD record
ord-915c8295fd5b49b69c681ccff0e55fae
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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