Oxalic Acid → HCID 9912205, compound

HRID 1666906Notes

Reaction equation

HRID 1666906 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.C(O[C:17](=O)[N:18]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([O:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:40]=1)[CH2:19][CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:28]=2)[NH:23][CH:22]=1)(C)(C)C.[OH-].[Na+].C(O)(=O)C(O)=O>O.C1COCC1>[CH2:31]([O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:20][CH2:19][N:18]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([O:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:40]=1)[CH3:17])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 14798Sodium HydroxideHCID 67443661HCID 67443661, compoundHCID 68718528lithium aluminium hydride THF

Product 1

HCID 9912205HCID 9912205, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine 1.0 M solution of LiAlH4-THF (13.4 ml, 13.4 mmol) and (3-phenoxy-benzyl)-(2-(5-benzyloxy-1H-indol-3-yl)-ethyl)-carbamic acid tert-butyl ester (1.83 g, 3.34 mmol) and slowly add 15 mL dry THF. After addition, heat the reaction mixture to reflux. After 4.5 h, cool down to room temperature. Quench the reaction by adding water (1.5 mL) cautiously, followed by 10% NaOH. Filter off the suspension and wash repeatedly with ether. Dry the organic solution over Na2SO4 and concentrate the solvent in vacuo. Purification by silica gel chromatography using CH2Cl2/MeOH as eluent to give the free base: 1H NMR (300 MHz, CDCl3) 2.35 (s, 3H), 2.69-2.74 (m, 2H), 2.91-2.96 9 m, 2H), 3.65 (s, 2H), 5.07 (s, 2H), 6.90-7.53 (m, 18H), 7.80 (s, 1H). This compound reacted further with oxalic acid to form the salt.

Workup

  1. additionAfter addition
  2. temperatureheat the reaction mixture
  3. temperatureto reflux
  4. customQuench
  5. customthe reaction
  6. filtrationFilter off the suspension
  7. washwash repeatedly with ether
  8. dry with materialDry the organic solution over Na2SO4
  9. concentrationconcentrate the solvent in vacuo
  10. customPurification by silica gel chromatography
  11. customto give the free base
  12. customto form the salt

Sources & evidence

ORD record
ord-720d6d2bd81c4b73a27447673603a206
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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