Ethylmorpholine → HCID 131712173, compound

HRID 1903864Notes

Reaction equation

HRID 1903864 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-ethyl-morpholine 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-aa48b795838a4c07a99548fe7a5d8131
Source dataset
uspto-grants-1984_03
Patent number
US04438103

Reaction notes

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