Hydrochloric Acid → Boc-Ser-Ala-OMe

HRID 247510

Reaction equation

HRID 247510 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 wtih 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% (13.33 Pa 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% potassium sulfate/bisulfate solution (3 times), saturated sodium bicarbonate (5 times). The solution is dried over Na2 `SO4 and evaporated to dryness. An oil is obtained which is dried to constant weight (30° C.13.33 Pa)

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% (13.33 Pa 35° C.)
  6. customThe oil obtained
  7. washthe product is washed with a solution of saturated sodium chloride (twice), 5% potassium sulfate/bisulfate solution (3 times), saturated sodium bicarbonate (5 times)
  8. customThe solution is dried over Na2 `SO4
  9. customevaporated to dryness
  10. customAn oil is obtained which
  11. customis dried to constant weight (30° C.13.33 Pa)

Sources & evidence

ORD record
ord-cd5963390008495b87f3373df184b3d6
Source dataset
uspto-grants-1987_11
Patent number
US04707541

Linked notes

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