4-Methylmorpholine → HCID 11616671, compound

HRID 1395824Notes

Reaction equation

HRID 1395824 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[NH2:32][C@H:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:34][OH:35]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH:32][C@H:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:34][OH:35])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 11616671HCID 11616671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

21.5 g of t-butoxycarbonylproline are dissolved in 500 ml of methylene chloride. The solution is cooled to -70° C. 20.2 g of N-methylmorpholine are added, followed by the addition of 13.7 g of isobutylchloroformate. The reaction mixture is warmed up to -15° C. and again cooled to -70° C. 15.6 g of methyl serinate hydrochloride are added to the reaction mixture which is stirred for sixteen hours at room temperature. The reaction mixture is extracted three times with 1 M potassium bisulfate, three times with a saturated solution of potassium bicarbonate and two times with brine. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and stripped of solvent. The product is purified by chromatography on silica gel to give methyl t-butoxycarbonylprolylserinate.

Workup

  1. temperatureThe reaction mixture is warmed up to -15° C.
  2. temperatureagain cooled to -70° C
  3. extractionThe reaction mixture is extracted three times with 1 M potassium bisulfate, three times with a saturated solution of potassium bicarbonate and two times with brine
  4. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f8cd474b96034e0a96418c566f96f777
Source dataset
uspto-grants-1980_05
Patent number
US04204991

Reaction notes

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