Hydrochloric Acid → [1,8-Diethyl-4-(methanesulfonyl-hydrazono)-1,3,4,9-tetrahydro-pyrano [3,4-b] indol-1-yl]-acetic acid methyl ester

HRID 1955723Notes

Reaction equation

HRID 1955723 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=O)[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19].CO.Cl.[CH3:27][S:28]([NH:31][NH2:32])(=[O:30])=[O:29]>O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[N:32][NH:31][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 269268MethanesulfonohydrazideHCID 11120627Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

Product 1

HCID 137231681[1,8-Diethyl-4-(methanesulfonyl-hydrazono)-1,3,4,9-tetrahydro-pyrano [3,4-b] indol-1-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the ester of Example 4, Step B (0.5 g, 1.6 mmol) was added 10 ml MeOH, 0.4 ml 1N HCl and 0.37 ml H2O. The mixture was stirred one minute followed by addition of CH3SO2NHNH2 all at once. After overnight stirring, the MeOH was evaporated and additional water was added. This aqueous phase was twice extracted with CH2Cl2. The organic phase was concentrated to a crude solid and purified by flash chromatography using CH2Cl2 --EtOAc 95-5 as eluent. The product 0.33 g, was obtained as a solid m.p. 80°-82° C.

Workup

  1. stirringAfter overnight stirring
  2. customthe MeOH was evaporated
  3. additionadditional water was added
  4. extractionThis aqueous phase was twice extracted with CH2Cl2
  5. concentrationThe organic phase was concentrated to a crude solid
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e3a1e0b2809a438e82c3009c0ae2160f
Source dataset
uspto-grants-1998_07
Patent number
US05776967

Reaction notes

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