1,2-Dichloroethane → HCID 66611998, compound

HRID 2204718Notes

Reaction equation

HRID 2204718 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.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]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:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[O:5])=[CH:7][C:8]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=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 8083MorpholineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66610949HCID 66610949, compound

Product 1

HCID 66611998HCID 66611998, 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), morpholine (0.13 ml, 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. 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 (SiO2, 1:1 cyclohexane/ethyl acetate) gave the title compound as an orange solid. 381 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 (SiO2, 1:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-dc863f37c334442cab489f326ced53f9
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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