Acetyl chloride → HCID 20637914, compound

HRID 342408Notes

Reaction equation

HRID 342408 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:13]3[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:12]=3[CH2:11][C@@H:10]3[C:21](=[O:30])[N:22]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:23][C:24](=[O:25])[N:9]23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C1COCC1>[C:38]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:13]3[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:12]=3[CH2:11][C@@H:10]3[C:21](=[O:30])[N:22]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:23][C:24](=[O:25])[N:9]23)=[CH:4][CH:3]=1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20637915HCID 20637915, compound

Product 1

HCID 20637914HCID 20637914, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 98 (0.2 g) in THF (15 mL) was added triethylamine (76 μL) and acetyl chloride (39 μL) and the resulting solution was stirred at room temperature for 2 hours. After evaporation of THF, the resulting residue was taken up in CH2Cl2 (100 mL), washed with water (2×50 mL) and dried over Na2SO4. After evaporation of CH2Cl2, the resulting solid was recrystallised from MeOH/H2O to give the title compound as a cream powder (120 mg) m.p. : 246° C.

Workup

  1. customAfter evaporation of THF
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of CH2Cl2
  5. customthe resulting solid was recrystallised from MeOH/H2O

Sources & evidence

ORD record
ord-07434daadf884d018c2adccdc07f1bc1
Source dataset
uspto-grants-1999_01
Patent number
US05859006

Reaction notes

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