Ethylmorpholine → Boc-(D)Ala-Gly-OBzl

HRID 1903865Notes

Reaction equation

HRID 1903865 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([OH:6])=O)[CH3:3].C(N1CCOCC1)C.C(OC(Cl)=O)C(C)C.[CH2:30]([O:37][C:38](=[O:41])[CH2:39][NH2:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O>O1CCCC1.CN(C=O)C>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([NH:40][CH2:39][C:38]([O:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:41])=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 7525Ethylmorpholine2×HCID 62365Isobutyl chloroformateHCID 637606BOC-D-alanineHCID 124082031HCID 124082031, compound

Product 1

HCID 15567200Boc-(D)Ala-Gly-OBzl

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.9 g of Boc-(D)Ala-OH and 1.3 ml of N-ethylmorpholine are dissolved in 50 ml of absolute tetrahydrofuran and 1.3 ml of chloroformic acid iso-butyl ester added dropwise at a temperature of -15°. After 5 minutes, a solution of 3.4 g of glycine-benzylester-tosylate and 1.3 ml of N-ethylmorpholine in 50 ml of DMF is added. After 1 hour's stirring at -10°, the reaction mixture is evaporated and the residue taken up in acetic acid. The solution is repeatedly washed with dilute citric acid and potassium bicarbonate. The title compound is crystallised from ether. M.P. 88°.

Workup

  1. customthe reaction mixture is evaporated
  2. washThe solution is repeatedly washed with dilute citric acid and potassium bicarbonate
  3. customThe title compound is crystallised from ether

Sources & evidence

ORD record
ord-dc6f42968a364588b273152e97690ea0
Source dataset
uspto-grants-1984_03
Patent number
US04438103

Reaction notes

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