1,2-Dichloroethane → HCID 71062325, compound

HRID 529004Notes

Reaction equation

HRID 529004 reaction equation
[CH2:1]([N:5]([CH2:42][CH2:43][CH2:44][CH3:45])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=2[C:30]([N:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].C(Cl)CCl.[CH2:50](O)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[CH2:42]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:29]=[CH:28][C:24]([C:25]([O:27][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:26])=[CH:23][C:22]=2[C:30]([N:32]2[CH2:41][CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33]2)=[O:31])[N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=1)=[O:7])[CH2:43][CH2:44][CH3:45]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 71062543HCID 71062543, compound

Product 1

HCID 71062325HCID 71062325, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid (320 mg, 0.96 mmol) in dry DCM (5.0 mL) was added EDC (932 mg, 4.81 mmol), benzyl alcohol (208 mg, 1.92 mmol) and DMAP (235 mg, 1.92 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 16 h. The reaction mixture was diluted with water and extracted with DCM (2×). The combined organic layer was dried over Na2SO4 and concentrated in vacuo to give crude product. The crude material was purified by flash chromatography (gradient 10 to 30% EtOAc/hexanes) to provide the title compound (400 mg, 92%). MS(ESI+) m/z 723.6 (M+H)+.

Workup

  1. extractionextracted with DCM (2×)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give crude product
  5. customThe crude material was purified by flash chromatography (gradient 10 to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0e425ab7b960495f8f83bc7945aa89a7
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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