Hydrochloric Acid → Z-Ser(But)-Ser(But)-OMe

HRID 1904033Notes

Reaction equation

HRID 1904033 reaction equation
[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:9]([OH:11])=O)[CH2:3][O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl.[NH2:23][C@H:24]([C:31]([O:33][CH3:34])=[O:32])[CH2:25][O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:9]([NH:23][C@H:24]([C:31]([O:33][CH3:34])=[O:32])[CH2:25][O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:11])[CH2:3][O:4][C:5]([CH3:6])([CH3:7])[CH3:8]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1715617Z-Ser(tBu)-OHHCID 7018830(S)-Methyl 2-amino-3-(tert-butoxy)propanoate

Product 1

HCID 131713446Z-Ser(But)-Ser(But)-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4.43 g of Z-Ser(But)-OH and 3.18 g of HCl.H-Ser(But)-OMe in 30 ml of dimethylformamide are added at 0° 1.89 ml of N-ethylmorpholine, 2.29 g of HOBt and 3.4 g of dicyclohexylcarbodiimide. After standing for 2 hours at 0° and for 15 hours at 20°, the resulting product is filtered off, the filtrate is concentrated by evaporation and taken up in ethyl acetate. After extraction of the solution with sodium bicarbonate, dilute hydrochloric acid and water, the solution is concentrated by evaporation to leave as oil Z-Ser(But)-Ser(But)-OMe; Rf (toluene/acetone 1:1)=0.70.

Workup

  1. filtrationthe resulting product is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. extractionAfter extraction of the solution with sodium bicarbonate, dilute hydrochloric acid and water
  4. concentrationthe solution is concentrated by evaporation

Sources & evidence

ORD record
ord-648a931901cb4480963112ae3a3deab9
Source dataset
uspto-grants-1984_03
Patent number
US04439425

Reaction notes

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