Phosgene → HCID 66971415, compound

HRID 1361311Notes

Reaction equation

HRID 1361311 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:28]([NH:30][CH2:31][CH2:32][OH:33])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.C(Cl)(Cl)=O>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:27])[C:23]([CH3:26])([CH3:24])[CH3:25])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:28]1[O:33][CH2:32][CH2:31][N:30]=1)([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 66971369HCID 66971369, compound

Product 1

HCID 66971415HCID 66971415, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

The product of Step A, (2S,4S)-1-Boc-2-{[(2-hydroxyethyl)amino]carbonyl}-4-[dimethylpropanoyl(4,4-dimethylcyclohexyl)amino]pyrrolidine (410 mg, 0.58 mmol) together with DMAP (70.7 mg, 0.58 mmol) and DIPEA (0.39 ml, 2.32 mmol) were dissolved in toluene (3 ml), and phosgene (20% in toluene, 0.31 ml, 0.87 mmol) was added dropwise. After the reaction solution was stirred at 30˜40° C. for 48 h, the solution was concentrated in vacuo. The residue was diluted with EtOAc, and washed with a saturated NaHCO3 aqueous solution, water and 1N HCl. The organic solution was dried over MgSO4, concentrated in vacuo, and the residue was purified by column chromatography (eluent: EtOAc) to give the title compound (160 mg, 62%).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with a saturated NaHCO3 aqueous solution, water and 1N HCl
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography (eluent: EtOAc)

Sources & evidence

ORD record
ord-1edd6dbccb764f27ba348e22c98ef01d
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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