Ethyl Acetate → tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate

HRID 2298003Notes

Reaction equation

HRID 2298003 reaction equation
[CH2:1]1[O:34][C:33]2[CH:32]=[CH:31][C:5]([CH2:6][N:7]([S:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([O:28][CH3:29])=[CH:23][C:22]=3[CH3:30])(=[O:20])=[O:19])[C@H:8]([CH2:16][NH2:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=2[O:2]1.C[Si](C#N)(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C(OCC)(=O)C>C(#N)C>[CH2:1]1[O:34][C:33]2[CH:32]=[CH:31][C:5]([CH2:6][N:7]([S:18]([C:21]3[C:22]([CH3:30])=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[CH3:27])(=[O:20])=[O:19])[C@H:8]([CH2:16][NH:17][S:42]([CH3:41])(=[O:44])=[O:43])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 82115Trimethylsilyl cyanideHCID 69762296tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate

Product 1

HCID 18337582tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionateYield 122.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate (1.02 g, 2.0 mmol), with trimethylsilyl cyanide (0.7 ml, 5.2 mmol) in dry acetonitrile (15 ml) was added methanesulfonyl chloride (0.18 ml, 2.3 mmol) and the material was stirred overnight. Ethyl acetate (80 ml) was added and the material was partitioned with aqueous hydrochloric acid (1.5%, 80 ml). The organic phase was collected and washed with an equal volume of brine. The aqueous phases were back extracted with ethyl acetate (2×80 ml) and the organic phases combined, dried (MgSO4), filtered and condensed to provide tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate as a pale yellow semi-viscous oil (1.4 g).

Workup

  1. customthe material was partitioned with aqueous hydrochloric acid (1.5%, 80 ml)
  2. customThe organic phase was collected
  3. washwashed with an equal volume of brine
  4. extractionThe aqueous phases were back extracted with ethyl acetate (2×80 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customcondensed

Sources & evidence

ORD record
ord-90a3f867ad914828b39482d357985805
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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