Diisopropylethylamine → HCID 69880680, compound

HRID 352921Notes

Reaction equation

HRID 352921 reaction equation
[C:1]([CH2:4][C@H:5]1[CH2:10][N:9]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:24])[CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:8][C@H:7]([CH2:25][C:26](O)=[O:27])[N:6]1[C:29](=[O:42])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)=[CH:32][CH:31]=1)(O)=[O:2].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[OH:27][CH2:26][CH2:25][C@H:7]1[CH2:8][N:9]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:24])[CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:10][C@H:5]([CH2:4][CH2:1][OH:2])[N:6]1[C:29](=[O:42])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=2)=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 4311764Sodium borohydrideHCID 69880407HCID 69880407, compound

Product 1

HCID 69880680HCID 69880680, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In tetrahydrofuran (40 ml), trans-2,6-bis(carboxymethyl)-4-[(6-chloronaphthalen-2-yl)sulfonyl]-1-[4-(pyridin-4-yl)benzoyl]piperazine (269 mg) was suspended, followed by the addition of N,N-diisopropylethylamine (480 μl) and 1-benzotriazolyloxy-tris(pyrrolidino)phosphonium hexafluorophosphate (672 mg) under ice cooling. The resulting mixture was stirred for 3.5 hours at room temperature. Under ice cooling, sodium borohydride (297 mg) was added and the resulting mixture was stirred for 15 hours at room temperature. The reaction mixture was ice cooled and added with water and ethyl acetate to separate the organic layer. The organic layer thus obtained was washed with aqueous NaCl solution, dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (4% methanol—dichloromethane), followed by dissolution in tetrahydrofuran. Saturated hydrochloride in methanol was added to the resulting solution and the resulting mixture was concentrated to dryness. Ethyl acetate was then added to the residue to crystallize the same, whereby the title compound was obtained.

Workup

  1. stirringthe resulting mixture was stirred for 15 hours at room temperature
  2. temperaturecooled
  3. customto separate the organic layer
  4. customThe organic layer thus obtained
  5. washwas washed with aqueous NaCl solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe residue obtained
  8. distillationby distilling off the solvent under reduced pressure
  9. customwas purified by chromatography on a silica gel column (4% methanol—dichloromethane)
  10. dissolutionfollowed by dissolution in tetrahydrofuran
  11. additionSaturated hydrochloride in methanol was added to the resulting solution
  12. concentrationthe resulting mixture was concentrated to dryness
  13. additionEthyl acetate was then added to the residue
  14. customto crystallize the same, whereby the title compound
  15. customwas obtained

Sources & evidence

ORD record
ord-98627549a83d4a408ae4d4a8e9fa4a94
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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