Dichloromethane → HCID 68814412, compound

HRID 732603Notes

Reaction equation

HRID 732603 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([CH:14]([OH:24])[CH:15]([NH2:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]2[CH:25]([CH2:26][O:27][CH3:28])[CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37].ClCCl>O1CCCC1.O>[C:1]([O:5][C:6]([N:8]1[CH:13]([CH:14]([OH:24])[CH:15]([NH:23][C:36](=[O:38])[CH3:37])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]2[CH:25]([CH2:26][O:27][CH3:28])[CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68818204HCID 68818204, compound

Product 1

HCID 68814412HCID 68814412, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 3-(2-amino-1-hydroxy-3-phenylpropyl)-7-methoxymethyl-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.243 mg, 0.622 mmol) in tetrahydrofuran (3 mL) and cool the mixture in an ice bath. Add triethylamine (0.091 mL, 0.653 mmol) and acetic anhydride (0.059 mL, 0.622 mmol) in tetrahydrofuran (2 mL). Stir the mixture at room temperature for 1 h. Add dichloromethane (30 mL) and water (10 mL). Separate layers and wash the organic layer with 0.5 N HCl, saturated aqueous sodium bicarbonate, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 3-5% isopropyl alcohol/47-45% dichlormethane in 50% hexanes) to give the title compound Isomer-1 (0.044 g, 16%) and Isomer-2 (0.077 mg, 29%).

Workup

  1. temperaturecool the mixture in an ice bath
  2. washSeparate layers and wash the organic layer with 0.5 N HCl, saturated aqueous sodium bicarbonate
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 3-5% isopropyl alcohol/47-45% dichlormethane in 50% hexanes)

Sources & evidence

ORD record
ord-8e9998fd0e4149c48b4e7183fec8ca50
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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