Ethylmorpholine → Z-Thr(But)-Ser(But)OH

HRID 2057851Notes

Reaction equation

HRID 2057851 reaction equation
C(N1CCOCC1)C.[NH:9]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C@H:10]([C:18]([O:20]N1C(=O)CCC1=O)=O)[C@@H:11]([CH3:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].[NH2:38][C@H:39]([C:46]([OH:48])=[O:47])[CH2:40][O:41][C:42]([CH3:45])([CH3:44])[CH3:43]>CN(C)C=O>[NH:9]([C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[C@H:10]([C:18]([NH:38][C@H:39]([C:46]([OH:48])=[O:47])[CH2:40][O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:20])[C@@H:11]([CH3:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 7525EthylmorpholineHCID 7004940(2S)-2-amino-3-(tert-butoxy)propanoic acid3×HCID 13503275Z-Thr(tBu)-OSU

Product 1

HCID 129820266Z-Thr(But)-Ser(But)OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.8 ml (0.1 mole) of N-ethylmorpholine and 40.6 g (0.1 mole) of Z-Thr(But)-OSu (Hoppe Seyler's Z. Physiol. Chem. 346, 60 (1966)) are added at 0° C. to a suspension of 16.1 g (0.1 mole) of H-Ser(But)-OH (Chem. Ber. 97, 2490 (1964)) in 100 ml of dimethylformamide. The mixture is then stirred for 5 hours at room temperature and is left to stand overnight at room temperature. The product is checked for the presence of H-Ser(But)-OH by thin layer chromatography. If no H-Ser(But)-OH is detectable by this method, any undissolved matter is filtered off. The filtrate is concentrated and the residue is partitioned between ether and 110 ml of 1 N citric acid. The ether phase is washed once more with 100 ml of 0.5 N citric acid and then with water or NaCl solution until neutral. The ether phase is then dried over Na2SO4 and is concentrated, and the product is dried in a high vacuum. Yield 32.5 g of an amorphous product (72%).

Workup

  1. waitis left
  2. waitto stand overnight at room temperature
  3. filtrationany undissolved matter is filtered off
  4. concentrationThe filtrate is concentrated
  5. customthe residue is partitioned between ether and 110 ml of 1 N citric acid
  6. washThe ether phase is washed once more with 100 ml of 0.5 N citric acid
  7. dry with materialThe ether phase is then dried over Na2SO4
  8. concentrationis concentrated
  9. customthe product is dried in a high vacuum

Sources & evidence

ORD record
ord-9a4b4cbf4a9b480a81bf43d17c8dd5e4
Source dataset
uspto-grants-1980_07
Patent number
US04212796

Reaction notes

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