4-Methylmorpholine → HCID 131712959, compound

HRID 1758465Notes

Reaction equation

HRID 1758465 reaction equation
ClC(OCC(C)C)=O.CN1CCOCC1.[C:16]([N:23]([CH3:29])[C@H:24]([C:26]([OH:28])=O)[CH3:25])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].Cl.C[O:32][C:33](=[O:44])[C@H:34]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[NH2:35]>C(OCC)(=O)C>[N:23]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])([CH3:29])[C@H:24]([C:26]([NH:35][C@H:34]([C:33]([OH:44])=[O:32])[CH2:36][C:37]1[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=1)=[O:28])[CH3:25]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 76956Methyl tyrosinate hydrochlorideHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid

Product 1

HCID 131712959HCID 131712959, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1 liter of ethyl acetate under nitrogen is cooled to between -5° and 0° C. and isobutyl chloroformate (37.6 ml, 290 mmole) is added followed by N-methylmorpholine (31.9 ml, 290 mmole). A sticky white solid forms and after 10 minutes BOC-N-methylalanine (58.9 grams, 290 mmoles) is added. A more granular solid forms and after 20 minutes tyrosine methylesterhydrochloride (57.93 grams, 250 mmoles) is added. Additional N-methylmorpholine (27.9 ml, 250 mmoles) is then added to obtain a pH of about 8. After 2.5 hours of stirring the mixture is washed three times with 500 ml of 1 N sodium bicarbonate and three times with 500 ml of 0.5 molar citric acid and dried over sodium sulfate. The reaction mixture is concentrated in vacuo affording the following crops of crystalline materials:

Workup

  1. customto obtain a pH of about 8
  2. washis washed three times with 500 ml of 1 N sodium bicarbonate and three times with 500 ml of 0.5 molar citric acid
  3. dry with materialdried over sodium sulfate
  4. concentrationThe reaction mixture is concentrated in vacuo
  5. customaffording the following crops of crystalline materials

Sources & evidence

ORD record
ord-40995bcf0eb1484e95286ed769c6f7d8
Source dataset
uspto-grants-1983_02
Patent number
US04374060

Reaction notes

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