Water → HCID 58288531, compound

HRID 1969083Notes

Reaction equation

HRID 1969083 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=2[CH2:20][N:21]([C:31]([O:33][CH3:34])=[O:32])[C@@H:22]([CH3:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=1)[CH3:2].C(N(CC)CC)C.[C:43](Cl)(=[O:45])[CH3:44].O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:43](=[O:45])[CH3:44])=[CH:15][C:14]=2[CH2:20][N:21]([C:31]([O:33][CH3:34])=[O:32])[C@@H:22]([CH3:30])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 58288541HCID 58288541, compound

Product 1

HCID 58288531HCID 58288531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To [3-(4-amino-2-{[methoxycarbonyl-((S)-1-methyl-2-phenyl-ethyl)-amino]-methyl}-phenoxy)-phenyl]-acetic acid ethyl ester (0.156 g, 0.33 mmol) and triethylamine (0.07 mL, 0.49 mmol) in CH2Cl2 (2 mL) was added acetyl chloride (0.02 mL, 0.33 mmol), and the reaction was stirred at room temperature for 2 minutes. LCMS analysis showed some starting material remained, so additional acetyl chloride (0.01 mL) was added, and the reaction was stirred for 30 minutes, until no starting material was seen by analytical LCMS. The mixture was worked-up with CH2Cl2 and H2O, and the organic layer was dried and concentrated to give the title compound.

Workup

  1. stirringthe reaction was stirred for 30 minutes, until no starting material
  2. customthe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b6097d3442494036972f291a3f3efa87
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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