alpha-Methyltryptophan → HCID 68849237, compound

HRID 2275397

Reaction equation

HRID 2275397 reaction equation
[CH3:1][C:2]([C:14](O)=[O:15])([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[NH2:3]>C1COCC1>[NH2:3][C:2]([CH3:1])([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[CH2:14][OH:15]

Participants

3

Reactant 1

HCID 95438alpha-Methyltryptophan

Product 1

HCID 68849237HCID 68849237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of alpha-methyl-DL-tryptophan (100 mg) in dry THF (10 ml) was added a borane-tetrahydrofuran complex (1.14 ml) dropwise. The reaction mixture was heated at 65° C. for 4.5 hours. The reaction mixture was quenched with ethanol (3 ml). The reaction mixture was concentrated and extracted with ethyl acetate and water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by preparative HPLC eluting with acetonitrile and water. The pure fractions were collected and freezedried.

Workup

  1. customThe reaction mixture was quenched with ethanol (3 ml)
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC
  8. washeluting with acetonitrile and water
  9. customThe pure fractions were collected
  10. customfreezedried

Sources & evidence

ORD record
ord-0fb0c1dc1df1450daeb532bb4f95ee12
Source dataset
uspto-grants-2015_09
Patent number
US09127007B2

Linked notes

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