Dichloromethane → HCID 11547406, compound

HRID 2085703Notes

Reaction equation

HRID 2085703 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:32][S:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=O)OC(C)(C)C)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[CH2:41]Cl>C(O)(C(F)(F)F)=O>[CH3:41][N:24]([CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]([NH:18][C:16](=[O:17])[O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:32][S:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 11642436HCID 11642436, compound

Product 1

HCID 11547406HCID 11547406, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 124B (1.36 g, 2.4 mmol) in dichloromethane (5 mL) and TFA (5 mL) was stirred at room temperature for 30 minutes, and concentrated. The concentrate was dissolved in acetic acid (1 mL) and 37% aqueous formaldehyde (5 mL), treated with 1M NaCNBH3 in THF (10 mL), stirred for 30 minutes, adjusted to pH 7 with aqueous NaHCO3, and extracted with ethyl acetate(3×100 mL). The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 48:48:4 ethyl acetate/dichloromethane/methanol to provide the desired product. MS (ESI) m/e 475 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in acetic acid (1 mL)
  3. addition37% aqueous formaldehyde (5 mL), treated with 1M NaCNBH3 in THF (10 mL)
  4. extractionextracted with ethyl acetate(3×100 mL)
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 48:48:4 ethyl acetate/dichloromethane/methanol

Sources & evidence

ORD record
ord-709eebaf8d0f43629ec556bd8126fdfa
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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