3,5-Dimethylbenzyl bromide → HCID 10298040, compound

HRID 2250978Notes

Reaction equation

HRID 2250978 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([NH:15]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[C:9]([OH:13])=[C:8]([Br:14])[CH:7]=1.[CH3:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([CH3:33])[CH:32]=1)[CH2:28]Br>>[NH2:15][CH:4]([CH2:5][C:6]1[CH:7]=[C:8]([Br:14])[C:9]([O:13][CH2:24][C:25]2[CH:26]=[C:27]([CH3:28])[CH:30]=[C:31]([CH3:33])[CH:32]=2)=[C:10]([Br:12])[CH:11]=1)[C:3]([OH:2])=[O:23]

Participants

3

Reactant 2

HCID 1413343,5-Dimethylbenzyl bromideHCID 14631438HCID 14631438, compound

Product 1

HCID 10298040HCID 10298040, compoundYield 35%

Procedure

Methyl-2-tert-butoxycarbonylamino-3-(3,5-dibromo-4-hydroxyphenyl)-propionate (0.20 g, 0.44 mmol) was coupled with 3,5-dimethyl benzylbromide (0.22 g, 1.1 mmol), using the method described in Example 2. After deprotection and final purification on HPLC, using the same conditions as described in Example 1(b), 70 mg (35%) of 2-amino-3-[3,5-dibromo-4-(3,5-dimethylbenzyloxy)phenyl]propionic acid was obtained. LC-MS (electrospray): m/z 458 (M+1).

Workup

  1. customAfter deprotection and final purification on HPLC

Sources & evidence

ORD record
ord-a7402d041db84428ba0391ef45781757
Source dataset
uspto-grants-2008_01
Patent number
US07319096B2

Reaction notes

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