Trifluoroacetic acid → HCID 131714601, compound

HRID 246917Notes

Reaction equation

HRID 246917 reaction equation
[NH2:1][C@H:2]([C:5]([NH:7][C@H:8]([C:10]([O:12][CH3:13])=[O:11])[CH3:9])=[O:6])[CH2:3][OH:4].C(O)(C(F)(F)F)=O.[NH:21]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:22]([C:27](O)=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.C(Cl)(Cl)Cl.CCOCC.CCCCCC.O>[NH:21]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[C@H:22]([C:27]([NH:1][C@H:2]([C:5]([NH:7][C@H:8]([C:10]([O:12][CH3:13])=[O:11])[CH3:9])=[O:6])[CH2:3][OH:4])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

10

Reactant 4

HCID 6422Trifluoroacetic acidHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 101958431HCID 101958431, compound

Product 1

HCID 131714601HCID 131714601, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

40 g of H-Ser-Ala-OMe, TFA and 32.9 g of Boc-Leu-OH, H2O are dissolved in 400 ml of DMF. The product is cooled with an ice bath with magnetic stirring and 14.4 ml of NEM then 65.8 g of BOP and enough NEM to maintain the pH at 6.5-7 are added. The product is stirred for 2 hrs. at ambient temperature. After monitoring by TLC, the product is evaporated to dryness (0.1 mm-35°) and the oil obtained is dissolved in 1500 ml of chloroform, washed twice with a saturated NaCl solution, three times with 5% sulfate/potassium bisulfate, 3 times with saturated sodium bicarbonate, dried over Na2SO4, evaporated to dryness (30°-water-jet pump). The oil obtained is solidified in ether: Fraction A=29 g. A second jet B is obtained by addition of hexane, identical in TLC: B=13.7 g.

Workup

  1. temperatureThe product is cooled with an ice bath
  2. additionare added
  3. stirringThe product is stirred for 2 hrs
  4. customat ambient temperature
  5. customthe product is evaporated to dryness (0.1 mm-35°)
  6. customthe oil obtained
  7. washwashed twice with a saturated NaCl solution, three times with 5% sulfate/potassium bisulfate, 3 times with saturated sodium bicarbonate
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness (30°-water-jet pump)
  10. customThe oil obtained

Sources & evidence

ORD record
ord-bc9ff4ddb91944ae9156040876a199c3
Source dataset
uspto-grants-1987_11
Patent number
US04704450

Reaction notes

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