Water → 4-(Benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester

HRID 444713Notes

Reaction equation

HRID 444713 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:1]([O:5][C:6]([CH:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 687248414-Benzylamino-cyclohexanecarboxylic acid tert-butyl ester

Product 1

HCID 687254864-(Benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl esterYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester (630 mg, 2.180 mmol) in DMF (20 mL) is added t-butyl bromoacetate (1 mL, 6.856 mmol) and Cs2CO3 (1.0 g, 3.069 mmol). The mixture stirs for 2 h. Then H2O (50 mL) is added the mixture is extracted with EtOAc (2×100 mL), dried with sodium sulfate and concentrated. The resulting solid is purified by flash chromatography (gradient elution: 0-20% EtOAc/Hep) which affords 300 mg of 4-(benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.24 (m, 5 H), 1.38 (m, 18 H), 1.86 (m, 4 H), 2.09 (m, 1 H), 3.14 (m, 2 H), 3.71 (m, 2 H), 7.29 (m, 5 H).

Workup

  1. extractionis extracted with EtOAc (2×100 mL)
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated
  4. customThe resulting solid is purified by flash chromatography (gradient elution: 0-20% EtOAc/Hep) which

Sources & evidence

ORD record
ord-72b62785338849809cd646c9d5eeec49
Source dataset
uspto-grants-2013_07
Patent number
US08476224B2

Reaction notes

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