Methanol → HCID 20675275, compound

HRID 244259Notes

Reaction equation

HRID 244259 reaction equation
C(=O)([O-])[O-].[K+].[K+].O.CO.C([O:13][C@@H:14]1[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@:17]([CH2:46][O:47][S:48]([C:51]2[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][CH:52]=2)(=[O:50])=[O:49])([CH2:27][O:28][Si:29]([C:42]([CH3:45])([CH3:44])[CH3:43])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:16][C@H:15]1[N:58]1[CH:65]=[C:64]([CH3:66])[C:62](=[O:63])[NH:61][C:59]1=[O:60])(=O)C>C(O)(=O)C>[CH2:20]([O:19][C@@H:18]1[C@@:17]([CH2:46][O:47][S:48]([C:51]2[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][CH:52]=2)(=[O:49])=[O:50])([CH2:27][O:28][Si:29]([C:42]([CH3:44])([CH3:43])[CH3:45])([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:16][C@@H:15]([N:58]2[CH:65]=[C:64]([CH3:66])[C:62](=[O:63])[NH:61][C:59]2=[O:60])[C@@H:14]1[OH:13])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 20675273HCID 20675273, compound

Product 1

HCID 20675275HCID 20675275, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium carbonate (12.75 mg, 0.0923 mmol) and water (0.5 ml) were added, under cooling with ice, to a methyl alcohol solution (4 ml) of Compound 35 (250 mg, 0.308 mmol), and the mixture was stirred for 22 hours at room temperature. Under cooling with ice, acetic acid was added to the reaction mixture to neutralize it, whereafter the solvent was distilled off under reduced pressure. After water was added to the residue, the mixture was extracted with ethyl acetate. The organic phase was washed with a saturated sodium chloride solution, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and then the resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 3:2) to obtain a white powder, Compound 36 (216.7 mg, 0.283 mmol, 92%). mp. 74-77° C. [α]D23 +5.15° (c=1.23, CHCl3). IR ν max (KBr): 3048, 2934, 1695, 1363, 1181, 1108, 977, 819, 704 cm−1.

Workup

  1. additionwas added to the reaction mixture
  2. distillationwhereafter the solvent was distilled off under reduced pressure
  3. additionAfter water was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 3:2)

Sources & evidence

ORD record
ord-7b5f75da7c48496b9daadae9c07cc21f
Source dataset
uspto-grants-2014_02
Patent number
USRE044779E1

Reaction notes

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