Water → HCID 54182257, compound

HRID 1464628Notes

Reaction equation

HRID 1464628 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH:23]2[CH:28]([CH:29]([CH3:31])[CH3:30])[CH2:27][CH2:26][CH:25]([CH3:32])[CH2:24]2)=[O:21])=[CH:15][CH:14]=1.Br[CH:34]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CC(C)([O-])C.[K+].O>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([CH:34]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:20]([O:22][CH:23]2[CH:28]([CH:29]([CH3:31])[CH3:30])[CH2:27][CH2:26][CH:25]([CH3:32])[CH2:24]2)=[O:21])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 16992BromocycloheptaneHCID 23665647Potassium tert-butoxideHCID 53640004HCID 53640004, compound

Product 1

HCID 54182257HCID 54182257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.3 kg of the compound from Example 6 are stirred with exclusion of moisture at -5° C. to +5° C. with 580 g of bromocycloheptane in 2.4 l of DMF. During the course of about 2 hours, a solution of 400 g of potassium tert-butoxide in 1.6 l of DMF is added. The mixture is stirred for a further 4 hours between -20° C. and -10° C. and 7.5 l of water are then added, during the course of which the title compound precipitates as a crude product. The crude product is centrifuged off, dried at 50° C. in vacuo and recrystallised twice using 6 l of ligroin; the solution is filtered hot in the first recrystallisation.

Sources & evidence

ORD record
ord-2323d358073b4062b62b9a547649d37e
Source dataset
uspto-grants-1994_04
Patent number
US05306820

Reaction notes

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