4-Methylmorpholine → Acetylalanylalanylprolyl-2-azaalanyl-l-lactic acid ethyl ester

HRID 461782Notes

Reaction equation

HRID 461782 reaction equation
[C:1]([NH:4][C@H:5]([C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=O)=[O:13])[CH3:11])=[O:8])[CH3:6])(=[O:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:37]([O:39][C:40](=[O:49])[C@:41]([C:44](=[O:48])[N:45]([CH3:47])[NH2:46])([CH3:43])[OH:42])[CH3:38]>O1CCCC1>[CH2:37]([O:39][C:40](=[O:49])[C@:41]([C:44](=[O:48])[N:45]([CH3:47])[NH:46][C:16](=[O:18])[C@@H:15]1[CH2:19][CH2:20][CH2:21][N:14]1[C:12](=[O:13])[C@H:10]([CH3:11])[NH:9][C:7](=[O:8])[C@H:5]([CH3:6])[NH:4][C:1](=[O:3])[CH3:2])([CH3:43])[OH:42])[CH3:38]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 12895631AcetylalanylalanylprolineHCID 1317109772-Azaalanyl-l-lactic acid ethyl ester

Product 1

HCID 131710978Acetylalanylalanylprolyl-2-azaalanyl-l-lactic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of acetylalanylalanylproline (0.66 mole) and N-methylmorpholine (0.66 mole) in dry tetrahydrofuran (25 ml) at -20° to -25° is added isobutylchloroformate (0.66 mmole). After 10 minutes a solution of 2-azaalanyl-l-lactic acid ethyl ester (0.66 mmole, example 3, step B) in tetrahydrofuran (2 ml) is added dropwise and the mixture is allowed to warm to room temperature over a period of 1 hour and stirred for a further 3 hours. The precipitate is removed by filtration, and the filtrate is concentrated to dryness. Chromatography of the residue on a silica gel (30 gm) and elution with 8% methanol in chloroform yields acetylalanylalanylprolyl-2-azaalanyl-l-lactic acid ethyl ester.

Workup

  1. customThe precipitate is removed by filtration
  2. concentrationthe filtrate is concentrated to dryness
  3. washChromatography of the residue on a silica gel (30 gm) and elution with 8% methanol in chloroform

Sources & evidence

ORD record
ord-911abafc4f944a37b2a6d9f5a8b1db09
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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