Triethylamine → HCID 59899169, compound

HRID 2227265Notes

Reaction equation

HRID 2227265 reaction equation
C([C@H]1COC(=O)N1[C:14]([C@H:16]([CH2:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1)[CH2:17][CH:18]=O)=[O:15])C1C=CC=CC=1.Cl.Cl.[CH3:30][O:31][C:32](=[O:47])[CH2:33][CH:34]([C:39]1[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=1)[CH2:35][CH2:36][CH2:37][NH2:38].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH3:30][O:31][C:32](=[O:47])[CH2:33][CH:34]([C:39]1[CH:40]=[N:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=1)[CH2:35][CH2:36][CH2:37][N:38]1[CH2:18][CH2:17][C@@H:16]([CH2:20][CH2:21][C:22]2([CH3:27])[O:26][CH2:25][CH2:24][O:23]2)[C:14]1=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59899148HCID 59899148, compoundHCID 69959877HCID 69959877, compound

Product 1

HCID 59899169HCID 59899169, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 1-11 (530 mg, 1.41 mmol), 1-6(460 mg, 1.41 mmol) and triethylamine (0.59 mL, 4.24 mmol) in 1,2-dichloroethane (15 mL) was added sodium triacetoxyborohydride (449 mg, 2.12 mmol) and the mixture was stirred for 16 h. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography (silica gel, 3:0.3:0.3 to 8:0.8:0.8% ethanol/ammonium hydroxide/water in ethyl acetate) to give 1-12 as an inseparable mixture of diastereomers.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated at reduced pressure
  5. customThe resulting oil was purified by flash column chromatography (silica gel, 3:0.3:0.3 to 8:0.8:0.8% ethanol/ammonium hydroxide/water in ethyl acetate)
  6. customto give 1-12
  7. additionas an inseparable mixture of diastereomers

Sources & evidence

ORD record
ord-b86b083b9e3745cf9ccd75c4475f832b
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

Loading…