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

HRID 2058400Notes

Reaction equation

HRID 2058400 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 acid2×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 mol) of N-ethylmorpholine and 40.6 g (0.1 mol) of Z-Thr(But)-OSu (Hoppe Seyler's Z.Physiol. Chem. 346, page 60, (1966)) were added at 0° C. to a suspension of 16.1 g (0.1 mol) of H-Ser(But)-OH (Chem. Ber. 97, page 2490 (1964)) in 100 ml of dimethylformamide, the mixture was stirred for 5 hours at room temperature and left to stand at room temperature overnight. When no H-Ser(But)-OH could be detected by thin layer chromatography, undissolved matter, if any, was filtered off, the filtrate was concentrated and the residue was partitioned between ether and 110 ml of 1 N citric acid. The ethereal phase was washed once again with 100 ml of 0.5 N citric acid and then washed neutral with water or NaCl solution. The ethereal phase was dried over Na2SO4, concentrated and dried in a high vacuum. Yield 32.5 g of an amorphous product (72%).

Workup

  1. waitleft
  2. waitto stand at room temperature overnight
  3. filtrationif any, was filtered off
  4. concentrationthe filtrate was concentrated
  5. customthe residue was partitioned between ether and 110 ml of 1 N citric acid
  6. washThe ethereal phase was washed once again with 100 ml of 0.5 N citric acid
  7. washwashed neutral with water or NaCl solution
  8. dry with materialThe ethereal phase was dried over Na2SO4
  9. concentrationconcentrated
  10. customdried in a high vacuum

Sources & evidence

ORD record
ord-13e95d1598a74e3ebc2e368a49af745f
Source dataset
uspto-grants-1980_07
Patent number
US04215037

Reaction notes

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