Dichloromethane → HCID 19611595, compound

HRID 1602358Notes

Reaction equation

HRID 1602358 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:12]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[CH3:33][C:34](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:35].CCOC(C)=O.C(Cl)[Cl:64]>>[ClH:64].[C:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:34](=[O:35])[CH3:33])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 19611596HCID 19611596, compound

Product 1

HCID 19611595HCID 19611595, compound

Conditions

Temperature
0 °C

Procedure

To a solution of the amine 10 from Step 1 (41 mg, 0.125 mmol) in 2 mL of CH2Cl2 was added triethylamine (0.035 mL, 0.250 mmol). The solution was cooled to 0° C., and acetic anyhydride (0.012 mL, 0.125 mmol) was added. After 1 hour, the mixture was poured into EtOAc and washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. This material was purified by silica gel chromatography (70% acetone/hexane), taken up in CH2Cl2 and treated with 1 M HCl/ether solution, and concentrated in vacuo. The titled product hydrochloride 9 was isolated as a white solid.

Workup

  1. washwashed with sat. aq. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThis material was purified by silica gel chromatography (70% acetone/hexane)
  6. additiontreated with 1 M HCl/ether solution
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e598538380ea4378a5e9e7b5df25dcf8
Source dataset
uspto-grants-1999_11
Patent number
US05981562

Reaction notes

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