Dimethylamine → HCID 59072825, compound

HRID 1358480Notes

Reaction equation

HRID 1358480 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[C:17]([OH:19])=O)=O)(C)(C)C.[CH2:20]([N:22](CC)[CH2:23]C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CNC>C(Cl)Cl>[CH3:20][N:22]([CH3:23])[C:17]([C@@H:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8]1)=[O:19]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2755955(2S)-1-(tert-Butoxycarbonyl)-2,3-dihydro-1H-indole-2-carboxylic acid

Product 1

HCID 59072825HCID 59072825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5 g of (2S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-indole-2-carboxylic acid (commercial) and of 5.8 g of triethylamine in 100 ml of DCM is cooled in an ice bath, 8.4 g of BOP are added and the mixture is left stirring for 15 minutes. Dimethylamine gas is then added by sparging for 10 minutes and the mixture is left stirring for 3 hours at AT. The reaction mixture is concentrated under vacuum, the residue is extracted with AcOEt, the organic phase is washed with water, with a 5% Na2CO3 solution and with a 5% KHSO4 solution and dried over Na2SO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with a DCM/AcOEt (85/15, v/v) mixture. 4.1, g of the expected product are obtained.

Workup

  1. waitthe mixture is left
  2. customby sparging for 10 minutes
  3. waitthe mixture is left
  4. stirringstirring for 3 hours at AT
  5. concentrationThe reaction mixture is concentrated under vacuum
  6. extractionthe residue is extracted with AcOEt
  7. washthe organic phase is washed with water, with a 5% Na2CO3 solution and with a 5% KHSO4 solution
  8. dry with materialdried over Na2SO4
  9. customthe solvent is evaporated under vacuum
  10. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-a1af8d3e5bee4a4289787baa3c639429
Source dataset
uspto-grants-2003_07
Patent number
US06596732B2

Reaction notes

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