Benzoyl chloride, 3,4-dichloro- → HCID 68466753, compound

HRID 453481Notes

Reaction equation

HRID 453481 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:9][C:8]=2[CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][C:38]=1[Cl:39])[C:33](Cl)=[O:34].C(N(CC)C(C)C)(C)C>C(Cl)Cl.O>[C:23]([O:22][C:20]([NH:19][CH2:18][C:8]1[CH:9]=[C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:12][C:7]=1[O:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:38]([Cl:39])=[C:30]([Cl:29])[CH:31]=2)=[CH:28][CH:27]=1)=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 81531DiisopropylethylamineHCID 68466596HCID 68466596, compound

Product 1

HCID 68466753HCID 68466753, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(4-(4-aminophenoxy)-3-((tert-butoxycarbonyl)aminomethyl)phenyl)acetate (100 mg, 0.259 mmol) was diluted with methylene chloride (3 mL) followed by the addition of 3,4-dichlorobenzoyl chloride (81.3 mg, 0.388 mmol) and N,N-diisopropylethyl amine (0.0451 mL, 0.259 mmol). The reaction was stirred for 3 hours. The reaction mixture was diluted with methylene chloride and water. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 12i eluting with hexanes:ethyl acetate (3:1) to yield 130 mg of methyl 2-(3-((tert-butoxycarbonyl)aminomethyl)-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetate.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified
  6. washeluting with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-37d623cf74c34454bd423fa788e9a534
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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