1,2-Dichloroethane → HCID 70026646, compound

HRID 1862724Notes

Reaction equation

HRID 1862724 reaction equation
OC(C(F)(F)F)=O.[C:8]1([CH2:14][CH2:15][CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:23][N:24]([CH:33]1[CH2:37][CH:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:35]([CH:44]=O)[CH2:34]1)[C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)(=O)C.C(N(CC)C(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:73]CCCl>>[ClH:73].[CH3:23][N:24]([CH:33]1[CH2:37][CH:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:35]([CH2:44][N:20]2[CH2:19][CH2:18][CH:17]([CH2:16][CH2:15][CH2:14][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:22][CH2:21]2)[CH2:34]1)[C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 6

HCID 111,2-Dichloroethane2×HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 88116354HCID 88116354, compoundHCID 131723820HCID 131723820, compound

Product 1

HCID 70026646HCID 70026646, compound

Procedure

To a 13×100 mm threaded vial can be added 4-(3-phenylprop-1-yl)piperidine-TFA salt (0.093 mmol). A solution of 1-(RS)-(N-(methyl)-N-(benzoyl)amino)-3-(SR)-(formyl)-4-(SR)-phenylcyclopentane (19 mg, 0.062 mmol) from Step D (derived from the higher Rf isomer in Step C) and acetic acid (0.006 mL, 0.1 mmol) in 1,2-dichloroethane (1 mL) can then be added to the vial. Sequentially, N,N-diisopropylethylamine (0.022 mL, 0.126 mmol) and a solution of sodium triacetoxyborohydride (26 mg, 0.123 mmol) in 1,2-dichloroethane (2 mL) are then added. The vial is sealed with a septum cap, gently shaken and stored at ambient temperature. After 18 hours, solvent is removed by a stream of warm nitrogen and the residue is redissolved in 80% acetonitrile in water. The sample can be purified on a Gilson Combinatorial Chromatography system using a 9.4 mm×25 cm Zorbax SB-C18 column. Fractions are collected based on the UV absorption and analyzed by mass spec to identify the title compound fractions. These are combined and evaporated.

Workup

  1. additioncan then be added to the vial
  2. customThe vial is sealed with a septum
  3. customcap
  4. customstored at ambient temperature
  5. customsolvent is removed by a stream of warm nitrogen
  6. dissolutionthe residue is redissolved in 80% acetonitrile in water
  7. customThe sample can be purified on a Gilson Combinatorial Chromatography system
  8. customFractions are collected
  9. custombased on the UV absorption
  10. customevaporated

Sources & evidence

ORD record
ord-bdf596114c3b4569916562185a957538
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

Loading…