Cesium carbonate → (RS)-3-(2-oxo-3-trityl-2,3-dihydro-benzooxazol-6-yl-sulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1280741Notes

Reaction equation

HRID 1280741 reaction equation
Br[C:2]1[CH:30]=[CH:29][C:5]2[N:6]([C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:37]([O:41][C:42]([N:44]1[CH2:48][CH2:47][CH:46]([SH:49])[CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38]>C1(C)C=CC=CC=1>[C:37]([O:41][C:42]([N:44]1[CH2:48][CH2:47][CH:46]([S:49][C:2]2[CH:30]=[CH:29][C:5]3[N:6]([C:10]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:7](=[O:9])[O:8][C:4]=3[CH:3]=2)[CH2:45]1)=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 30970186-Bromo-3-trityl-3H-benzooxazol-2-oneHCID 13324658tert-Butyl 3-sulfanylpyrrolidine-1-carboxylate

Product 1

HCID 69927165(RS)-3-(2-oxo-3-trityl-2,3-dihydro-benzooxazol-6-yl-sulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tris(dibenzylideneacetone)dipalladium chloroform complex (14 mg, 13.5 □mol) and 1,1′-bis(diphenylphosphino)ferrocene (30 mg, 54.1 □mol) in degassed and dry toluene (2 ml) were stirred at room temperature until the solution turned orange (15 minutes). 6-Bromo-3-trityl -3H-benzooxazol-2-one (0.2 g, 0.44 mmol), Cs2CO3 (0.22 g, 0.68 mmol) and (RS) -3-mercapto-pyrrolidine-1-carboxylic acid tert-butyl ester (0.1 g, 0.49 mmol) in toluene (0.5 ml) were successively added. After 4 hours stirring at 100° C., the reaction mixture was cooled to room temperature and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1 then 1:1) to provide (RS)-3-(2-oxo-3-trityl-2,3-dihydro-benzooxazol-6-yl-sulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.19 g 7 77%) as a white foam, MS: m/e=596.1 (M+NH4+).

Workup

  1. customTris(dibenzylideneacetone)dipalladium chloroform complex (14 mg, 13.5 □mol) and 1,1′-bis(diphenylphosphino)ferrocene (30 mg, 54.1 □mol) in degassed
  2. custom(15 minutes)
  3. stirringAfter 4 hours stirring at 100° C.
  4. temperaturethe reaction mixture was cooled to room temperature
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1

Sources & evidence

ORD record
ord-066352f0db224638871417928f4f2ec6
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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