Water → Nalpha-Trityl-S-(9H-xanthen-9-yl)-L-cysteine

HRID 19462Notes

Reaction equation

HRID 19462 reaction equation
[CH:1]1[C:14]2[CH:13]([S:15][CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[NH2:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.O.C(NCC)C.[C:28](Cl)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[C:28]([NH:18][C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][S:15][CH:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8021DiethylamineHCID 10566205S-(9H-Xanthen-9-yl)cysteine

Product 1

HCID 11214896Nalpha-Trityl-S-(9H-xanthen-9-yl)-L-cysteineYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
4 °C

Procedure

A sample of 1.0 g of S-(9H-Xanthen-9-yl)cysteine (3.3 mmole) from Example 4 was dissolved in 10 ml of chloroform. To the solution was added 1.5 ml of water and 1.5 ml of diethylamine. The mixture was cooled to 4° C. by an ice bath and 0.98 g of trityl chloride (3.5 mmole) was added in portions over a period of 30 min. After 2 h of stirring at room temperature. The reaction mixture was separated. The organic phase was washed twice with 4% diethylamine aqueous solution. The organic layer was dried over Na2SO4. The drying reagent was removed by filtration and the filtrate was condensed to dryness by rotary evaporation. The residue was refluxed in 10 ml of a 1:30 mixture of diethyl amine/ethyl alcohol. The resultant diethyl ammonium salt was partitioned between 10 ml of ethyl acetate and 7 ml of 5% aqueous KHSO4 and 7 ml of water. The ethyl acetate layer was separated and was dried over MgSO4 and was concentrated to get 1.4 g of product.

Workup

  1. customThe reaction mixture was separated
  2. washThe organic phase was washed twice with 4% diethylamine aqueous solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe drying reagent was removed by filtration
  5. customcondensed to dryness
  6. customby rotary evaporation
  7. temperatureThe residue was refluxed in 10 ml of a 1:30 mixture of diethyl amine/ethyl alcohol
  8. customThe resultant diethyl ammonium salt was partitioned between 10 ml of ethyl acetate and 7 ml of 5% aqueous KHSO4 and 7 ml of water
  9. customThe ethyl acetate layer was separated
  10. dry with materialwas dried over MgSO4
  11. concentrationwas concentrated

Sources & evidence

ORD record
ord-92954937813a4d2a95d4030fa83e8f21
Source dataset
uspto-grants-2010_06
Patent number
US07745392B2

Reaction notes

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