Water → HCID 58288474, compound

HRID 1969085Notes

Reaction equation

HRID 1969085 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].[CH3:36][S:37](Cl)(=[O:39])=[O:38].C(N(CC)CC)C.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][S:37]([CH3:36])(=[O:39])=[O:38])=[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 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58288541HCID 58288541, compound

Product 1

HCID 58288474HCID 58288474, 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 (0.144 g, 0.3 mmol) and methanesulfonyl chloride (0.02 mL, 0.3 mmol) in CH2Cl2 (2 mL) was added triethylamine (0.08 mL, 0.6 mmol), and the reaction was stirred at room temperature for 1 hour. The mixture was worked-up with CH2Cl2 and H2O, and the organic layer was dried and concentrated. The residue was purified by silica gel chromatography (20-40% EtOAc in hexanes) to give the title compound.

Workup

  1. customthe organic layer was dried
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (20-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-839533fe6a194cb9b27e8c8189b732ca
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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