Ethylmorpholine → HCID 54368637, compound

HRID 1609620Notes

Reaction equation

HRID 1609620 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][C@H:7]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:5])[CH3:3].F[C:26]([C:29]([OH:31])=[O:30])(F)F.C(O[C:35](=O)[C:36]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(Br)CC)C.[CH2:47](N1CCOCC1)[CH3:48]>CC(N(C)C)=O>[CH2:18]([O:17][C:15]([CH:7]1[CH2:8][CH:9]2[CH:14]([CH2:13][CH2:12][CH2:11][CH2:10]2)[N:6]1[C:4](=[O:5])[C@H:2]([CH3:3])[NH:1][CH:26]([C:29]([O:31][CH2:47][CH3:48])=[O:30])[CH2:35][CH2:36][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 7525EthylmorpholineHCID 10468399HCID 10468399, compoundHCID 131717593HCID 131717593, compound

Product 1

HCID 54368637HCID 54368637, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

11.1 g of Ala-Oic-OBzl.TFA, 7 g of α-bromophenylbutyric acid ethyl ester and 3.3 ml of N-ethylmorpholine are stirred in 20 ml of dimethylacetamide for 4 days at room temperature. The mixture is concentrated to a large extent in vacuo, the residue is dissolved in methanol, the methanolic solution is adjusted to pH 2 with aqueous 2N HCl, and lipophilic compounds are extracted with petroleum ether. The methanolic phase is concentrated and 5% sodium carbonate solution is added to it, and the reaction product is extracted in ethyl acetate. Chromatography over silica gel (system ethyl acetate/petroleum ethe 5:3) yields the title compound as a colorless oil.

Workup

  1. concentrationThe mixture is concentrated to a large extent in vacuo
  2. dissolutionthe residue is dissolved in methanol
  3. extractionare extracted with petroleum ether
  4. concentrationThe methanolic phase is concentrated
  5. addition5% sodium carbonate solution is added to it
  6. extractionthe reaction product is extracted in ethyl acetate

Sources & evidence

ORD record
ord-d3c8d45d71dd4579b3ee24af311087a6
Source dataset
uspto-grants-1995_03
Patent number
US05401766

Reaction notes

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