Acetyl chloride → HCID 136197445, compound

HRID 539883Notes

Reaction equation

HRID 539883 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([C:12]2[CH:13]=[C:14]([NH:22][C:23]([CH2:25][CH2:26][CH2:27][NH:28][C:29](OC(C)(C)C)=[O:30])=[O:24])[CH:15]=[CH:16][C:17]=2[O:18][CH2:19][CH2:20][CH3:21])[NH:6][C:7](=[O:11])[C:8]=1[CH2:9][CH3:10])[CH3:2].F[C:37](F)(F)C(O)=O.C(Cl)(=O)C>ClCCl>[C:29]([NH:28][CH2:27][CH2:26][CH2:25][C:23]([NH:22][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH3:21])=[C:12]([C:5]2[NH:6][C:7](=[O:11])[C:8]([CH2:9][CH3:10])=[C:3]([CH2:1][CH3:2])[N:4]=2)[CH:13]=1)=[O:24])(=[O:30])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 135890168HCID 135890168, compound

Product 1

HCID 136197445HCID 136197445, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (200 mg, 0.412 mmol) of example 106 was dissolved in dichloromethane (30 ml) and added with trifluoroacetic acid (2 ml), followed by stirring at room temperature for 0.5 h. The reaction mixture was directly concentrated to dryness. The resultant oil was dissolved in dichloromethane (30 ml) and added with triethylamine (1 ml). Under ice-water both, acetyl chloride (33 mg, 0.42 mmol) was added dropwise thereinto. 0.5 h later, TLC showed that the reaction was complete. The reaction mixture was washed with water (50 ml) and saturated saline (50 ml). The organic layer was dried with anhydrous sodium sulfate, and concentrated, and the residue was passed through a silica gel column to give the white title compound (50 mg, yield: 28%). 1H NMR (CDCl3) δ: 8.79 (1H, br), 8.51 (1H, d), 7.93 (1H, dd), 6.99 (1H, d), 6.05 (1H, br), 4.15 (2H, t), 3.40 (2H, t), 2.68 (2H, q), 2.60 (2H, q), 2.44 (2H, t), 2.03 (3H, s), 1.97 (2H, m), 1.94 (2H, m), 1.32 (3H, t), 1.16 (3H, t), 1.14 (3H, t).

Workup

  1. concentrationThe reaction mixture was directly concentrated to dryness
  2. dissolutionThe resultant oil was dissolved in dichloromethane (30 ml)
  3. additionadded with triethylamine (1 ml)
  4. custom0.5 h
  5. washThe reaction mixture was washed with water (50 ml) and saturated saline (50 ml)
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-69e97c7ec57f4657a3b1a54c4b23c45a
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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