HCID 58746641, compound → HCID 58746795, compound

HRID 724708Notes

Reaction equation

HRID 724708 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C@@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[C:14]([Br:19])[CH:13]=1>C(O)(=O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C@@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[C:14]([Br:19])[CH:13]=1

Participants

3

Reactant 1

HCID 58746641HCID 58746641, compound

Product 1

HCID 58746795HCID 58746795, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of tert-butyl [(1S)-2-[(2-aminophenyl)amino]-1-(3-bromo-4-iodobenzyl)-2-oxoethyl]carbamate (640 mg, 1.14 mmol) in acetic acid (30.0 mL) was stirred at 40° C. for 2 h. The solution was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water, dried with sodium sulfate, filtered, and concentrated in vacuo to yield the desired product (610 mg, 98%). 1H NMR (400 MHz, CD3OD): δ 7.80 (d, 1H), 7.6 (m, 3H), 7.3 (m, 2H), 6.94 (d, 1H), 5.13 (m, 1H), 3.39 (m, 1H), 3.09 (m, 1H), 1.37 (s, 9H); LCMS found for C20H22BrIN3O2 (M+H)+: m/z=542, 544.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e3b879581e144c8b95cfce3b18dead1
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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