4-Methylmorpholine → HCID 13501990, compound

HRID 1981285Notes

Reaction equation

HRID 1981285 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:35][CH:36]1[CH:43]2[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:45][CH:37]1[CH2:38]3)[CH2:42]2>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([NH:35][CH:36]1[CH:37]2[CH2:45][CH:41]3[CH2:40][CH:39]([CH2:44][CH:43]1[CH2:42]3)[CH2:38]2)=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 253322-AminoadamantaneHCID 62365Isobutyl chloroformateHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 13501990HCID 13501990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (ca. -78°) solution of 106 g (0.4 mole) of t-butoxycarbonyl-L-phenylalanine (Boc-Phe) and 88 ml (ca. 0.8 mole) of N-methylmorpholine in 300 ml of dichloromethane, stirred over 30 g of 4 A molecular sieves, was added dropwise 52.4 ml (ca. 0.4 mole) of isobutyl chloroformate. The mixture was allowed to warm slowly to 5° and then recooled to about -78°. After adding 75 g (0.4 mole) of 2-aminoadamantane, the mixture was allowed to warm to room temperature and to stir overnight. The mixture was clarified by filtration and washed with several portions of 0.5M sodium bisulfate. The organic layer was heated at reflux over activated charcoal, filtered, dried over sodium sulfate, and concentrate in vacuo to dryness. The resultant title compound was used without further purification in subsequent reactions.

Workup

  1. temperatureto warm slowly to 5°
  2. customrecooled to about -78°
  3. filtrationThe mixture was clarified by filtration
  4. washwashed with several portions of 0.5M sodium bisulfate
  5. temperatureThe organic layer was heated
  6. temperatureat reflux over activated charcoal
  7. filtrationfiltered
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrate in vacuo to dryness
  10. customThe resultant title compound was used without further purification in subsequent reactions

Sources & evidence

ORD record
ord-60aa341baa6a42509b589848f655623c
Source dataset
uspto-grants-1985_04
Patent number
US04514332

Reaction notes

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