Methyl chloroformate → HCID 69257509, compound

HRID 1528680Notes

Reaction equation

HRID 1528680 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][N:15]=2)[N:6]=1.Cl[C:27]([O:29][CH3:30])=[O:28].C(OCC)(=O)C>N1C=CC=CC=1>[NH2:20][C:18]1[C:17]([NH:21][C:27](=[O:28])[O:29][CH3:30])=[CH:16][N:15]=[C:14]([N:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[C:5]([CH2:4][C:3]3[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=3[F:1])=[N:6]2)[N:19]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8857Ethyl AcetateHCID 67516926HCID 67516926, compound

Product 1

HCID 69257509HCID 69257509, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 330 mg (0.98 mmol) of the compound from example 12A were initially charged in pyridine (12 ml), the mixture was cooled to 0° C. and 84 μl (108 mmol) of methyl chloroformate were then added dropwise. The reaction mixture was stirred further at RT overnight, and ethyl acetate was then added. The organic phase was washed twice with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The residue was separated by preparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient), giving 241 mg (62% of theory) of the target compound as a colorless solid.

Workup

  1. washThe organic phase was washed twice with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was separated by preparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient)

Sources & evidence

ORD record
ord-d5b6fea3c33449d6a4ae55765dc34f10
Source dataset
uspto-grants-2015_07
Patent number
US09090609B2

Reaction notes

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