4-Methylmorpholine → Boc-AlaAlaPro-OBzl

HRID 437132Notes

Reaction equation

HRID 437132 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[CH2:30]([O:37][C:38](=[O:49])[C@@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:44](=[O:48])[C@H:45]([CH3:47])[NH2:46])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.C(Cl)(Cl)Cl>[CH2:30]([O:37][C:38](=[O:49])[C@@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:44](=[O:48])[C@H:45]([CH3:47])[NH:46][C:11](=[O:13])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 85082Tert-butoxycarbonylalanineHCID 13034412L-alanyl-L-proline, phenylmethyl ester, hydrochloride

Product 1

HCID 15289361Boc-AlaAlaPro-OBzl

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.035 mole of t-butyloxycarbonylalanine in 80 ml of dry tetrahydrofuran which has been cooled to -20° to - 30° is added 4 ml of N-methylmorpholine and then 4.6 ml of isobutylchloroformate. After stirring for 10 minutes there is added 0.035 mole of alanylproline benzylester hydrochloride and 4 ml of N-methylmorpholine in 60 ml of chloroform. The reaction mixture is stirred overnight at room temperature, concentrated in vacuo and the residue taken up between ethyl acetate and 0.25 N hydrochloric acid. The organic layer is separated, washed with saturated sodium bicarbonate, water, dried over magnesium sulfate and concentrated in vacuo to give t-butoxycarbonylalanylalanylproline benzyl ester.

Workup

  1. stirringThe reaction mixture is stirred overnight at room temperature
  2. concentrationconcentrated in vacuo
  3. customThe organic layer is separated
  4. washwashed with saturated sodium bicarbonate, water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fba2d27d39e4c91a3e0612c097bcf54
Source dataset
uspto-grants-1977_06
Patent number
US04029772

Reaction notes

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