Diethylamine → HCID 69529809, compound

HRID 1796413Notes

Reaction equation

HRID 1796413 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21](O)=[O:22])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69529788HCID 69529788, compound

Product 1

HCID 69529809HCID 69529809, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g (0.009 mole) of (2S)-2-tert-butoxycarbonylamino-7-hydroxycarbonylmethoxy-tetralin, 0.93 ml of N,N-diethylamine (0.009 mole), 4 g (0.009 mole) of BOP and 1.9 ml (0.0135 mole) of triethylamine in 90 ml of anhydrous DMF were stirred at ambient temperature for 6 hours. The solvent was evaporated off and the residue was taken up in ethyl acetate. It was washed with a sodium bicarbonate solution. An emulsion was obtained which was filtered over celite. The filtered solution was washed with acetic acid and then with water. The organic phase was dried over sodium sulfate and the solvent was evaporated off under reduced pressure. The product was purified by flash chromatography, eluting with a 1:1 ethyl acetate/hexane mixture. The product of the heading was obtained in the form of a very dense oil.

Workup

  1. customThe solvent was evaporated off
  2. washIt was washed with a sodium bicarbonate solution
  3. customAn emulsion was obtained which
  4. filtrationwas filtered over celite
  5. washThe filtered solution was washed with acetic acid
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customthe solvent was evaporated off under reduced pressure
  8. customThe product was purified by flash chromatography
  9. washeluting with a 1:1 ethyl acetate/hexane mixture
  10. customThe product of the heading was obtained in the form of a very dense oil

Sources & evidence

ORD record
ord-f046675b9dd24665b97a8da73eb62585
Source dataset
uspto-grants-2006_04
Patent number
US07030160B2

Reaction notes

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