Water → HCID 86757711, compound

HRID 1250206Notes

Reaction equation

HRID 1250206 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@:15]23[CH2:24][C:23]4[N:25]=[C:26]5[C:31](=[CH:32][C:22]=4[CH2:21][C@H:20]2[CH2:19][N:18](C(OC=C)=O)[CH2:17][CH2:16]3)[CH:30]=[CH:29][CH:28]=[CH:27]5)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].O>CO.Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@:15]23[CH2:24][C:23]4[N:25]=[C:26]5[C:31](=[CH:32][C:22]=4[CH2:21][C@H:20]2[CH2:19][NH:18][CH2:17][CH2:16]3)[CH:30]=[CH:29][CH:28]=[CH:27]5)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86757712HCID 86757712, compound

Product 1

HCID 86757711HCID 86757711, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Conditions

Temperature
0 °C

Procedure

(4aR, 12aR)-4a-(3-benzyloxyphenyl)-2-vinyloxycarbonyl-1,2,3,4,4a,5,12,12a-octahydroquinolino[2, 3-g]isoquinoline (181 mg, 0.369 mmol) was dissolved in a 10% hydrogen chloride methanol solution (6 ml), and the resultant solution was heated under reflux for 1 hour. After the solution was cooled to 0°C., an aqueous saturated sodiumbicarbonate solution (30 ml) and water (150 ml) were added to the solution, followed by extraction with chloroform (200 ml, 2 times). The organic layers were dried, and then concentrated to obtain the target compound (155 mg). The thus-obtained compound was supplied to next reaction without purification.

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionfollowed by extraction with chloroform (200 ml, 2 times)
  3. customThe organic layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f3dc1dafe36149a59d2beb17eff2eaa4
Source dataset
uspto-grants-2002_01
Patent number
US06337330B1

Reaction notes

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