Potassium Carbonate → HCID 86602948, compound

HRID 901809Notes

Reaction equation

HRID 901809 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:46]([O:56][C@@H:57]2[O:124][C@H:123]([CH2:125][O:126]C(=O)C3C=CC=CC=3)[C@@H:78]([O:79][C@@H:80]3[O:112][C@H:111]([CH2:113][O:114]C(=O)C4C=CC=CC=4)[C@@H:101]([O:102]C(=O)C4C=CC=CC=4)[C@H:91]([O:92]C(=O)C4C=CC=CC=4)[C@H:81]3[O:82]C(=O)C3C=CC=CC=3)[C@H:68]([O:69]C(=O)C3C=CC=CC=3)[C@H:58]2[O:59]C(=O)C2C=CC=CC=2)[C@@H:45]([CH2:135][O:136][CH2:137][C:138]2[CH:143]=[CH:142][CH:141]=[CH:140][CH:139]=2)[O:44][C@@H:10]1[O:11][C@H:12]1[C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][N:14]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C@@H:13]1[CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:46]([O:56][C@@H:57]2[O:124][C@H:123]([CH2:125][OH:126])[C@@H:78]([O:79][C@@H:80]3[O:112][C@H:111]([CH2:113][OH:114])[C@@H:101]([OH:102])[C@H:91]([OH:92])[C@H:81]3[OH:82])[C@H:68]([OH:69])[C@H:58]2[OH:59])[C@@H:45]([CH2:135][O:136][CH2:137][C:138]2[CH:139]=[CH:140][CH:141]=[CH:142][CH:143]=2)[O:44][C@@H:10]1[O:11][C@H:12]1[C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][N:14]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C@@H:13]1[CH2:35][O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86602949HCID 86602949, compound

Product 1

HCID 86602948HCID 86602948, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (390.8 mg, 0.20 mmol) synthesized in Example 20 (20c) was dissolved in methanol (8 mL) and potassium carbonate (27.6 mg, 0.20 mmol) was added thereto, followed by stirring of the mixture at room temperature for 6 hours. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with saturated aqueous sodium hydrogencarbonate (10 mL) and saturated brine (10 mL). The mixture was neutralized with methanol-hydrochloric acid and the solvent was distilled off under reduced pressure. The residue was purified using silica gel flash column chromatography (methylene chloride:methanol, 30:1-20:1-10:1, V/V) to obtain the desired title compound (146.5 mg, 61%) as a colorless solid.

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate (10 mL) and saturated brine (10 mL)
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified

Sources & evidence

ORD record
ord-144d4fffd3b6402ba7c0c4c5c2ebedb0
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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