1,2-Dichloroethane → HCID 66611752, compound

HRID 2204696Notes

Reaction equation

HRID 2204696 reaction equation
[Br: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]([OH:6])=O.Br[C:30]1[C:31](C=O)=[CH:32][C:33](OCC2C=CC=CC=2)=C([CH:45]=1)C(OCC1C=CC=CC=1)=O.S(=O)(=O)(O)[NH2:57].CC(CC)=C.C(N(C(C)C)CC)(C)C.N1CCCCC1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([C:4]([N:57]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:45]2)=[O:6])=[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

12

Reactant 8

HCID 111,2-DichloroethaneHCID 5987Sulfamic AcidHCID 8082PiperidineHCID 112402-Methyl-1-buteneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66612057HCID 66612057, compoundHCID 86694927HCID 86694927, compound

Product 1

HCID 66611752HCID 66611752, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-5-[(phenylmethyl)oxy]-4-{[(phenylmethyl)oxy]carbonyl}benzoic acid (may be prepared as by oxidation of phenylmethyl 5-bromo-4-formyl-2-[(phenylmethyl)oxy]benzoate—may be prepared as described in Description 24—with sulfamic acid in the presence of 2-methyl-1-butene; 436 mg, 0.99 mmol) in N,N-dimethylformamide (5 ml) was added diisopropylethylamine (0.35 ml, 1.98 mmol), piperidine (0.15 ml, 1.48 mmol), 1-hydroxy-7-azabenzotriazole (188 mg, 1.38 mmol) and EDC (379 mg, 1.98 mmol). The solution was stirred for 18 hours. Ethyl acetate (10 ml) and water (10 ml) were added. The organic layer was separated and washed further with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane) gave the title compound as a white solid. 225 mg.

Workup

  1. custommay be prepared
  2. customThe organic layer was separated
  3. washwashed further with water (2×10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification by column chromatography (SiO2, 1:1 ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-562d618e734f46f99aba2380bb906355
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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