Morpholine → HCID 86753410, compound

HRID 1457238Notes

Reaction equation

HRID 1457238 reaction equation
N1CCOCC1.C([O:10][C:11](=[O:38])[C@:12]([S:25]([C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])([CH:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([OH:17])=[O:16])[NH2:13])C=C>C1COCC1.C(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:28]1([S:25]([C@@:12]([C:11]([OH:38])=[O:10])([CH:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([OH:17])=[O:16])[NH2:13])(=[O:26])=[O:27])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 86753411HCID 86753411, compound

Product 1

HCID 86753410HCID 86753410, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Morpholine (3.3 ml; 38 mmol) was added to a solution of 2-Naphthalenesulphonyl β-benzyl-L-aspartic acid allyl ester (3--3) (1.73 g; 3.8 mmol) and tetrakis (triphenylphosphine) palladium (0.42 g; 0.37 mmol) in dry THF (40 ml) under an atmosphere of argon. The reaction mixture was stirred at room temperature for 2 h and then evaporated to dryness. The resultant yellow oil was triturated with ethyl acetate followed by filtration of the white solid obtained. The crude product was dissolved in DCM (30 ml) and then washed successively with 2N HCl (30 ml) and brine (30 ml×3). The solution was dried (sodium sulphate). Filtration and evaporation of the solvent gave the product as a white solid.

Workup

  1. customevaporated to dryness
  2. customThe resultant yellow oil was triturated with ethyl acetate
  3. filtrationfollowed by filtration of the white solid
  4. customobtained
  5. washwashed successively with 2N HCl (30 ml) and brine (30 ml×3)
  6. dry with materialThe solution was dried (sodium sulphate)
  7. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-79f96ff56d8e41a09954023be117be31
Source dataset
uspto-grants-1998_12
Patent number
US05847125

Reaction notes

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