Methanol → HCID 21138126, compound

HRID 651509Notes

Reaction equation

HRID 651509 reaction equation
[F:1][C:2]([F:42])([C:38]([F:41])([F:40])[F:39])[CH2:3][CH2:4][CH2:5][S:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]1[CH2:35][C@@:33]2([CH3:34])[C@@H:29]([CH2:30][CH2:31][C@@H:32]2[OH:36])[C@H:28]2[C@H:19]1[C:20]1[CH:21]=[CH:22][C:23]([OH:37])=[CH:24][C:25]=1[CH2:26][CH2:27]2)(=[O:8])=[O:7].CN([C:46]1[CH:51]=CC=CN=1)C.C[OH:53].[C:54](OC(=O)C)(=[O:56])[CH3:55]>N1C=CC=CC=1>[C:54]([O:37][C:23]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:28]([C@H:29]4[C@@:33]([CH2:35][C@@H:18]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][S:6]([CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:42])[C:38]([F:39])([F:40])[F:41])(=[O:8])=[O:7])([CH3:34])[C@@H:32]([O:36][C:51](=[O:53])[CH3:46])[CH2:31][CH2:30]4)[CH2:27][CH2:26][C:25]=2[CH:24]=1)(=[O:56])[CH3:55]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 88111274HCID 88111274, compound

Product 1

HCID 21138126HCID 21138126, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.39 g of the product obtained in Example 61 in 16.6 cm3 of pyridine, 3.14 cm3 of acetic anhydride and 154 mg of dimethylaminopyridine are agitated for 45 minutes at ambient temperature. 5.4 cm3 of methanol is added, followed by agitation for 10 minutes, evaporating the solvents, the residue is taken up in ethyl acetate, followed by washing with an aqueous solution of M hydrochloric acid, then with sodium chloride, drying and evaporating the solvent. After chromatographing the residue on silica (eluant: ethyl acetate-cyclohexane 5-5 then 3-7), 3.25 g of expected product is obtained.

Workup

  1. customevaporating the solvents
  2. washby washing with an aqueous solution of M hydrochloric acid
  3. dry with materialwith sodium chloride, drying
  4. customevaporating the solvent

Sources & evidence

ORD record
ord-f05ac017e07340c0a67fcec0201d8198
Source dataset
uspto-grants-2001_08
Patent number
US06281204B1

Reaction notes

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