1,2-Dichloroethane → HCID 66612145, compound

HRID 2204716Notes

Reaction equation

HRID 2204716 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(C(C)C)CC)(C)C.[F:38][C:39]1([F:44])[CH2:43][CH2:42][NH:41][CH2:40]1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:4]([N:41]2[CH2:42][CH2:43][C:39]([F:44])([F:38])[CH2:40]2)=[O:5])=[CH:7][C:8]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:9]([CH:10]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27828273,3-DifluoropyrrolidineHCID 66610949HCID 66610949, compound

Product 1

HCID 66612145HCID 66612145, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-5-[(phenylmethyl)oxy]-4-{[(phenylmethyl)oxy]carbonyl}benzoic acid (may be prepared as described in Description 63; 480 mg, 1.21 mmol) in N,N-dimethylformamide (5 ml) was added diisopropylethylamine (0.63 ml, 3.63 mmol), 3,3-difluoropyrrolidine (208 mg, 1.45 mmol), 1-hydroxy-7-azabenzotriazole (198 mg, 1.45 mmol) and EDC (417 mg, 2.18 mmol). The solution was stirred for 18 hours, then water (10 ml) and ethyl acetate (15 ml) were added and the organic layer was separated. The organic layer was washed further with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (2:1-1:1 cyclohexane/ethyl acetate) gave the title compound as a orange solid. 444 mg.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed further with water (2×10 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification by column chromatography (2:1-1:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-38c38f53917a4afc8c073867ad9ba9ed
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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