4-Methylmorpholine → Boc-Pro-Ser-NH2

HRID 1703035Notes

Reaction equation

HRID 1703035 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.CN1CCOCC1.ClC(OCC)=O.[NH2:29][C@H:30]([C:33]([NH2:35])=[O:34])[CH2:31][OH:32]>O1CCCC1.CN(C)C=O.CO>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:29][C@H:30]([C:33]([NH2:35])=[O:34])[CH2:31][OH:32])=[O:5]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 101138L-Serinamide

Product 1

HCID 131712843Boc-Pro-Ser-NH2

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.00 g (4.65 mmoles) Boc-Pro-OH in 10 ml anhydrous tetrahydrofuran, 0.52 ml (4.65 mmoles) N-methylmorpholine, and 0.45 ml (4.65 mmoles) ethyl chloroformate are successively added at a temperature of -12° C. After stirring at this temperature for 2 minutes, a cold solution of 0.48 g (4.65 mmoles) H-Ser-NH2 (R. W. Hanson and H. N. Rydon, J. Chem. Soc., 836, 1964) in 10 ml dimethylformamide is added. The reaction mixture is stirred at -10° C. for 3 hours and at 20° C. for 1 hour, then filtered from salts and evaporated in vacuo. The residue is taken up with tetrahydrofuran, filtered, and the solution evaporated again in vacuo. By crystallization from methanol-diethylether 1.1 g of compound (1) are obtained: m.p. 138° C. [α]D25 -58.9° (c=1, MeOH); RfA =0.15; RfB =0.33.

Workup

  1. stirringThe reaction mixture is stirred at -10° C. for 3 hours and at 20° C. for 1 hour
  2. filtrationfiltered from salts
  3. customevaporated in vacuo
  4. filtrationfiltered
  5. customthe solution evaporated again in vacuo
  6. customBy crystallization from methanol-diethylether 1.1 g of compound (1)
  7. customare obtained

Sources & evidence

ORD record
ord-6c75fcebf0f4403398cda1c9056e86b0
Source dataset
uspto-grants-1982_09
Patent number
US04350627

Reaction notes

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