Hydrochloric Acid → tert-butyl 2(R)-(2,6-dimethyl-4-methoxybenzene sulfonylamino)-3-phthalimido-propionate

HRID 2298000Notes

Reaction equation

HRID 2298000 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@H:7]([NH2:20])[CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])([CH3:4])([CH3:3])[CH3:2].C[Si](C#N)(C)C.[CH3:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([CH3:37])[C:30]=1[S:38](Cl)(=[O:40])=[O:39].Cl>C(#N)C.C(OCC)(=O)C>[CH3:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([CH3:37])[C:30]=1[S:38]([NH:20][C@H:7]([CH2:8][N:9]1[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]2[C:13]1=[O:14])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21])(=[O:39])=[O:40]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 82115Trimethylsilyl cyanideHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 18337584tert-butyl-2(R)-amino-3-phthalimido-propionate

Product 1

HCID 18337577tert-butyl 2(R)-(2,6-dimethyl-4-methoxybenzene sulfonylamino)-3-phthalimido-propionateYield 71.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl-2(R)-amino-3-phthalimido-propionate (5.7 g, 19.63 mmol) in dry acetonitrile (60 ml) was added trimethylsilylcyanide (8.6 ml, 68.7 mmol). After 5 minutes 2,6-dimethyl-4-methoxybenzenesulfonyl chloride (4.84 g, 20.6 mmol) was added in one portion. The material was stirred at ambient temperature for 1 hour and then ethyl acetate (80 ml) was added and the mixture was transferred to a seperatory funnel. The organic phase was partioned with aqueous hydrochloric acid (1.5%, 100 ml), 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 (magnesium sulfate), filtered and condensed. The residue was chromatographed (flash silica gel, 30% ethyl acetate-hexanes) to provide tert-butyl 2(R)-(2,6-dimethyl-4-methoxybenzene sulfonylamino)-3-phthalimido-propionate as white semi-solid (6.9 g).

Workup

  1. customthe mixture was transferred to a seperatory funnel
  2. customcollected
  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 (magnesium sulfate)
  6. filtrationfiltered
  7. customcondensed
  8. customThe residue was chromatographed (flash silica gel, 30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-e2aed0e657e947fbb56ca33eaba0f7d1
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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