Sodium Bicarbonate → HCID 69908460, compound

HRID 382477Notes

Reaction equation

HRID 382477 reaction equation
[CH2:1]([CH:3]([CH2:48][CH3:49])[C:4]([O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:22][C@H:23]([N:25](C(OC(C)(C)C)=O)[CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH2:36][C:37]([F:40])([F:39])[F:38])[CH3:24])=[CH:16][C:17]=2[C:19](=[O:21])[NH2:20])[CH:12]=[CH:11]1)=[O:5])[CH3:2].C(=O)(O)[O-].[Na+]>Cl>[CH2:48]([CH:3]([CH2:1][CH3:2])[C:4]([O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:22][C@H:23]([NH:25][CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH2:36][C:37]([F:39])([F:38])[F:40])[CH3:24])=[CH:16][C:17]=2[C:19](=[O:21])[NH2:20])[CH:12]=[CH:11]1)=[O:5])[CH3:49]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69907473HCID 69907473, compound

Product 1

HCID 69908460HCID 69908460, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(R)-3-[5-[2-[N-(tert-Butoxycarbonyl)-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-7-carbamoyl-1H-indol-1-yl]propyl 2-ethylbutyrate (1.56 g) was dissolved in isopropano (10 ml), and concentrated hydrochloric acid (5.0 ml) was added dropwise to the solution under ice-cooling with stirring. After the mixture was stirred for 4 hours at room temperature, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel (eluent:methylene chloride/methanol=20/1) and recrystallized from diethyl ether-hexane to give (R)-3-[7-carbamoyl-5-[2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indol-1-yl]propyl 2-ethylbutyrate (1.10 g) as white crystals.

Workup

  1. additionwas added dropwise to the solution under ice-
  2. temperaturecooling
  3. stirringAfter the mixture was stirred for 4 hours at room temperature
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by column chromatography on silica gel (eluent:methylene chloride/methanol=20/1)
  10. customrecrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-b9676d97e7bc4ba4932e62215928b034
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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