Ethylmorpholine → HCID 131712173, compound

HRID 443915Notes

Reaction equation

HRID 443915 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N1CCOCC1)C.C(OC(Cl)=O)C(C)C.Cl.[NH2:37][C@H:38]([CH2:43][OH:44])[CH2:39][CH2:40][S:41][CH3:42]>O1CCCC1.CN(C)C=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:37][C@H:38]([CH2:43][OH:44])[CH2:39][CH2:40][S:41][CH3:42]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 22815435HCID 22815435, compound

Product 1

HCID 131712173HCID 131712173, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.9 g of Boc-Phe-OH and 1.4 ml of N-ethylmorpholine are dissolved in 50 ml of absolute tetrahydrofuran and 1.4 ml of chloroformic acid iso-butyl ester added at -10°. After 10 minutes, a solution of 1.7 g of methioninol-hydrochloride in 25 ml of dimethyl formamide is added. After two hours stirring at room temperature, the solution is evaporated under vacuum and the residue taken up in acetic acid. The solution is repeatedly washed with dilute citric acid and potassium bicarbonate and the title compound isolated. M.P. 106°.

Workup

  1. customthe solution is evaporated under vacuum
  2. washThe solution is repeatedly washed with dilute citric acid and potassium bicarbonate

Sources & evidence

ORD record
ord-e2e4b4dec50745df8421d875f9d750f6
Source dataset
uspto-grants-1981_04
Patent number
US04261888

Reaction notes

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