Dichloromethane → HCID 119057322, compound

HRID 2279457Notes

Reaction equation

HRID 2279457 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C@@H:27]2[CH2:31][CH2:30][CH2:29][NH:28]2)[NH:10][C:11]([N:13]2[CH2:22][CH2:21][C:20]3[CH:19]=[N:18][C:17]([NH:23][CH:24]([CH3:26])[CH3:25])=[N:16][C:15]=3[CH2:14]2)=[O:12])=[CH:5][C:4]=1[F:32].[CH3:33][C:34](OC(C)=O)=[O:35].C(Cl)Cl>O>[C:34]([N:28]1[CH2:29][CH2:30][CH2:31][C@H:27]1[C@H:9]([C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[C:4]([F:32])[CH:5]=1)[NH:10][C:11]([N:13]1[CH2:22][CH2:21][C:20]2[CH:19]=[N:18][C:17]([NH:23][CH:24]([CH3:25])[CH3:26])=[N:16][C:15]=2[CH2:14]1)=[O:12])(=[O:35])[CH3:33]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 131733483HCID 131733483, compound

Product 1

HCID 119057322HCID 119057322, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 83 and Ac2O (6.45 μL, 0.0683 mmol), TEA (25.9 μL, 0.186 mmol) and DCM (5 mL) was stirred for 1 h then poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:10) to afford 0.020 g (65.9%) of I-87: MS m/z (APCI-pos) M+1=489.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with DCM/MeOH (500:10)
  7. customto afford 0.020 g (65.9%) of I-87: MS m/z (APCI-pos) M+1=489

Sources & evidence

ORD record
ord-a24744ddf64946e098dbc48dc1c91184
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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