Hydrochloric Acid → Boc-Ser-Ala-OMe

HRID 246916Notes

Reaction equation

HRID 246916 reaction equation
[NH2:1][C@H:2]([C:4]([O:6][CH3:7])=[O:5])[CH3:3].Cl.[CH3:9][C:10]([O:13][C:14]([NH:16][C@H:17]([C:20](OCC1C=CC([N+]([O-])=O)=CC=1)=[O:21])[CH2:18][OH:19])=[O:15])([CH3:12])[CH3:11].ON1C2C=CC=CC=2N=N1>CN(C=O)C.C(Cl)(Cl)Cl>[NH:16]([C:14]([O:13][C:10]([CH3:12])([CH3:11])[CH3:9])=[O:15])[C@H:17]([C:18]([NH:1][C@H:2]([C:4]([O:6][CH3:7])=[O:5])[CH3:3])=[O:19])[CH2:20][OH:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 82335L-Alanine methyl esterHCID 11121352Boc-Ser-ONB

Product 1

HCID 131715374Boc-Ser-Ala-OMe

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

25 g of H-Ala-OMe, HCl and 66 g. of Boc-Ser-ONb are dissolved in 500 ml DMF. The product is cooled in an ice bath and 25 ml of NEM, 24 g of N-hydroxy benzotriazole are added with magnetic stirring and the pH is maintained at 6.5 or 7 by addition of NEM. The product is stirred for 18 hrs. at ambient temperature. After TLC monitoring, the medium is evaporated to 90% (0.1 mm Hg-35° C.). The oil obtained is dissolved in 1.500 ml of chloroform, the product is washed with a solution of saturated sodium chloride (twice), 5% sulfate/potassium bisulfate solution (3 times), saturated sodium bicarbonate (5 times). The solution is dried over Na2SO4 and evaporated to dryness. An oil is obtained which is dried to constant weight (30°-0.1 mm Hg).

Workup

  1. temperatureThe product is cooled in an ice bath
  2. temperaturethe pH is maintained at 6.5 or 7 by addition of NEM
  3. stirringThe product is stirred for 18 hrs
  4. customat ambient temperature
  5. customAfter TLC monitoring, the medium is evaporated to 90% (0.1 mm Hg-35° C.)
  6. customThe oil obtained
  7. washthe product is washed with a solution of saturated sodium chloride (twice), 5% sulfate/potassium bisulfate solution (3 times), saturated sodium bicarbonate (5 times)
  8. dry with materialThe solution is dried over Na2SO4
  9. customevaporated to dryness
  10. customAn oil is obtained which
  11. customis dried to constant weight (30°-0.1 mm Hg)

Sources & evidence

ORD record
ord-fb075386912c43159460710d9eb974e3
Source dataset
uspto-grants-1987_11
Patent number
US04704450

Reaction notes

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