Piperonyl alcohol → tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-phthalimido-propionate

HRID 1760809Notes

Reaction equation

HRID 1760809 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[S:11]([NH:14][C@H:15]([CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=[O:13])=[O:12].[CH2:35](O)[C:36]1[CH:44]=[CH:43][C:42]2[O:41][CH2:40][O:39][C:38]=2[CH:37]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[CH2:40]1[O:41][C:42]2[CH:43]=[CH:44][C:36]([CH2:35][N:14]([S:11]([C:3]3[C:2]([CH3:1])=[CH:7][C:6]([O:8][CH3:9])=[CH:5][C:4]=3[CH3:10])(=[O:12])=[O:13])[C@H:15]([CH2:23][N:24]3[C:25](=[O:34])[C:26]4=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]4[C:28]3=[O:29])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:37][C:38]=2[O:39]1

Participants

6

Reactant 4

HCID 10322Piperonyl alcoholHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 18337577tert-butyl 2(R)-(2,6-dimethyl-4-methoxybenzene sulfonylamino)-3-phthalimido-propionate

Product 1

HCID 18337583tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-phthalimido-propionateYield 97.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a cooled (ice bath) solution of tert-butyl 2(R)-(2,6-dimethyl-4-methoxybenzene sulfonylamino)-3-phthalimido-propionate (6.9 g, 14.12 mmol) in dry benzene (150 ml) with piperonyl alcohol (3.22 g, 21.2 mmol) and tributyl phosphine (5.3 ml, 21.2 mmol) was added 1,1′-(azodicarbonyl)-dipiperidine (5.35 g, 21.2 mmol). The mixture was allowed to warm to ambient temperature overnight. The material was loaded onto a flash silica gel column using ethyl acetate-hexanes (30%) as eluant, providing tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-phthalimido-propionate as a white solid (8.59 g).

Sources & evidence

ORD record
ord-ec34ce886f8540be936f61cdc17f17b2
Source dataset
uspto-grants-2005_01
Patent number
US06844366B2

Reaction notes

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