Acetic Anhydride → HCID 77737310, compound

HRID 50645Notes

Reaction equation

HRID 50645 reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:8][CH:7]([N:9]2[C:13]3[N:14]=[C:15]([S:29][CH2:30][CH2:31][CH3:32])[N:16]=[C:17]([N:18]([CH:20]4[CH2:22][CH:21]4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:19])[C:12]=3[N:11]=[N:10]2)[CH:6]([OH:33])[CH:5]1[OH:34].C(N(CC)C(C)C)(C)C.[C:44](OC(=O)C)(=[O:46])[CH3:45]>ClCCl>[OH:34][CH:5]1[CH:6]([OH:33])[CH:7]([N:9]2[C:13]3[N:14]=[C:15]([S:29][CH2:30][CH2:31][CH3:32])[N:16]=[C:17]([N:18]([CH:20]4[CH2:22][CH:21]4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:19])[C:12]=3[N:11]=[N:10]2)[CH2:8][CH:4]1[CH2:3][NH:2][C:44](=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 131724388HCID 131724388, compound

Product 1

HCID 77737310HCID 77737310, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 7 (0.2 g) in dichloromethane (15 ml) was treated with N,N-diisopropylethylamine (0.11 g) followed by acetic anhydride (0.16 g) and the resultant mixture was stirred at room temperature for 4 hours. The mixture was washed with a saturated solution of aqueous sodium bicarbonate (15 ml) and the organic layer concentrated in vacuo. The residue was dissolved in a 0.1 molar solution of sodium methoxide in methanol (20 ml) and the solution allowed to stand for 2 hours at room temperature. Following concentration in vacuo the residue was acidified by careful addition of acetic acid, the mixture was again concentrated in vacuo and he residue azeotroped with toluene (3×100 ml). Purification by chromatography (SiO2 methanol:chloroform 1:24 as eluant) gave the title compound (0.12 g).

Workup

  1. washThe mixture was washed with a saturated solution of aqueous sodium bicarbonate (15 ml)
  2. concentrationthe organic layer concentrated in vacuo
  3. dissolutionThe residue was dissolved in a 0.1 molar solution of sodium methoxide in methanol (20 ml)
  4. concentrationconcentration in vacuo the residue
  5. additionwas acidified by careful addition of acetic acid
  6. concentrationthe mixture was again concentrated in vacuo and he residue
  7. customazeotroped with toluene (3×100 ml)
  8. customPurification by chromatography (SiO2 methanol:chloroform 1:24 as eluant)

Sources & evidence

ORD record
ord-a10c7cc4277b4246845510112566a467
Source dataset
uspto-grants-2004_03
Patent number
US06713483B1

Reaction notes

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