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

HRID 1731231Notes

Reaction equation

HRID 1731231 reaction equation
[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@H:2]([C:10]([O:12]N1C(=O)CCC1=O)=O)[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[NH2:30][C@H:31]([C:38]([O:40][CH3:41])=[O:39])[CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35].Cl.C(OCC)(=O)C>C(N(CC)CC)C>[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[C@H:2]([C:10]([NH:30][C@H:31]([C:38]([O:40][CH3:41])=[O:39])[CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:12])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 7018830(S)-Methyl 2-amino-3-(tert-butoxy)propanoateHCID 13503275Z-Thr(tBu)-OSU

Product 1

HCID 131710554Z-Thr(But)-Ser(But)-OMe

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

16.25 g of Z-Thr(But)-OSu and 8.47 g of H-Ser(But)-OMe. HCl are added to 200 ml of ethyl acetate, 5.6 ml of triethylamine are added at 0°C and the solution is stirred for 15 hours at 20°C and washed with 1 N citric acid, 1 N sodium bicarbonate and water. After drying over sodium sulphate, the solution is evaporated, whereupon the product, which is pure according to thin layer chromatography, is obtained as an oil.

Workup

  1. additionare added at 0°C
  2. washwashed with 1 N citric acid, 1 N sodium bicarbonate and water
  3. dry with materialAfter drying over sodium sulphate
  4. customthe solution is evaporated, whereupon the product, which
  5. customis obtained as an oil

Sources & evidence

ORD record
ord-be6a612873934733895b42cd6419d82f
Source dataset
uspto-grants-1976_11
Patent number
US03994871

Reaction notes

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