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4-Methylmorpholine → Boc-Ala-Glu(OBzl)-OH

HRID 1764776
Notes
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Reaction equation

HRID 1764776 reaction equation
[NH2:1][C@H:2]([C:15]([OH:17])=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:18]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:19]([C:21](ON1C(=O)CCC1=O)=[O:22])[CH3:20].CN1CCOCC1>CN(C=O)C>[NH:18]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C@H:19]([C:21]([NH:1][C@H:2]([C:15]([OH:17])=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:22])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 122337L-Glutamic acid, 5-(phenylmethyl) esterHCID 11011585Boc-Ala-OSu

Product 1

HCID 124669052Boc-Ala-Glu(OBzl)-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

H-Glu(OBzl)-OH (7.0 g, 29.5 mmol) was finely ground in a mortar and pestle and then stirred with 8.88 g (32.3 mmol) of Boc-Ala-OSu for 48 hours in 250 ml DMF in the presence of 6 ml N-methylmorpholine (NMM). Some more NMM was added to maintain the reaction slightly basic during the reaction. The solvent was evaporated and the residue partitioned between 30 ml ethyl acetate and 500 ml H2O containing 2 ml of 10% H2SO4. The organic layer was then washed three times with water, dried(Na2SO4) and evaporated to dryness. The product was taken up in a small volume of ether and treated with a large volume of petroleum ether. A white amorphous solid was obtained which was homogeneous on tlc: Yield, 11.0 g (91.5%); mp 84°-88°; [α]D25 = -8.08° (c l, DMF).

Workup

  1. temperatureto maintain
  2. customthe reaction
  3. customslightly basic during the reaction
  4. customThe solvent was evaporated
  5. customthe residue partitioned between 30 ml ethyl acetate and 500 ml H2O containing 2 ml of 10% H2SO4
  6. washThe organic layer was then washed three times with water, dried(Na2SO4)
  7. customevaporated to dryness
  8. additiontreated with a large volume of petroleum ether
  9. customA white amorphous solid was obtained which
  10. customYield

Sources & evidence

ORD record
ord-4b00c66b007f4e359d101c294560c3b3
Source dataset
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04116951

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes