Glycol monoacetate → N-(2-Acetoxyethyl)-N-[2-(4-benzyloxycarbonylpiperazinyl)-1-(p-methoxybenzyl)ethyl]-5-isoquinolinesulfonamide

HRID 1587196Notes

Reaction equation

HRID 1587196 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([NH:28][S:29]([C:32]2[C:33]3[CH:34]=[CH:35][N:36]=[CH:37][C:38]=3[CH:39]=[CH:40][CH:41]=2)(=[O:31])=[O:30])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42]([O:45][CH2:46][CH2:47]O)(=[O:44])[CH3:43].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:42]([O:45][CH2:46][CH2:47][N:28]([CH:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH2:17][N:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15]1)[S:29]([C:32]1[C:33]2[CH:34]=[CH:35][N:36]=[CH:37][C:38]=2[CH:39]=[CH:40][CH:41]=1)(=[O:31])=[O:30])(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 10960Glycol monoacetateHCID 11776TriphenylphosphineHCID 19795884N-[2-(4-benzyloxycarbonylpiperazinyl)-1-(p-methoxybenzyl)ethyl]-5-isoquinolinesulfonamide

Product 1

HCID 19796392N-(2-Acetoxyethyl)-N-[2-(4-benzyloxycarbonylpiperazinyl)-1-(p-methoxybenzyl)ethyl]-5-isoquinolinesulfonamideYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of the product obtained in Example 73 was dissolved in 5 ml of tetrahydrofuran, to the solution were added 220 mg of ethylene glycol monoacetate and 685 mg of triphenylphosphine in place of N-tert-butoxycarbonylethanolamine, according to the procedure described :n Example 136, to obtain 600 mg of the title compound in a colorless amorphous form.

Sources & evidence

ORD record
ord-01d2aa9bbc4846129b822b753ff5f06d
Source dataset
uspto-grants-1993_06
Patent number
US05216150

Reaction notes

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