Water → HCID 14372935, compound

HRID 2107053Notes

Reaction equation

HRID 2107053 reaction equation
C([Li])C[CH2:3][CH3:4].C(OC([C:12]1[N:13]=[CH:14][C:15]2[N:16](S(C3C=CC(C)=CC=3)(=O)=O)[C:17]3[C:22]([C:23]=2[C:24]=1[CH2:25][O:26][CH3:27])=[CH:21][C:20]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH:19][CH:18]=3)=O)(C)C.[OH2:46]>C1COCC1>[C:3]([C:12]1[N:13]=[CH:14][C:15]2[NH:16][C:17]3[C:22]([C:23]=2[C:24]=1[CH2:25][O:26][CH3:27])=[CH:21][C:20]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH:19][CH:18]=3)(=[O:46])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 53671227HCID 53671227, compoundHCID 178418339Butyllithium

Product 1

HCID 14372935HCID 14372935, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under an N2 atmosphere, 45 mmol of n-butyl-lithium is added dropwise within 10 minutes to 3.70 g (22 mmol) of methanesulfine-p-toluidide in 100 ml of dry THF at -78° C. To this mixture is added 5.58 g (10 mmol) of 6-benzyloxy-4-methoxymethyl-9-tosyl-β-carboline-3-carboxylic acid isopropyl ester, dissolved in 50 ml of dry THF. The reaction mixture assumes a dark-blue color. The mixture is stirred for one hour at -78° C., poured into water, and extracted with ether. The ether is drawn off and the remaining oil is dissolved in 100 ml of methanol. Then 5 g of KOH is added and the mixture agitated under reflux for one hour. After cooling, ice water is added and the precipitate is filtered off. Yield: 3.5 g.

Workup

  1. extractionextracted with ether
  2. dissolutionthe remaining oil is dissolved in 100 ml of methanol
  3. additionThen 5 g of KOH is added
  4. stirringthe mixture agitated
  5. temperatureunder reflux for one hour
  6. temperatureAfter cooling
  7. additionice water is added
  8. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-ba27c1521b1940c1b6e3c6ad8ae5a45d
Source dataset
uspto-grants-1990_06
Patent number
US04933345

Reaction notes

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