Hydrochloric Acid → HCID 86627957, compound

HRID 251730Notes

Reaction equation

HRID 251730 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O.Cl>C1COCC1.O>[C:22]([O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86627958HCID 86627958, compound

Product 1

HCID 86627957HCID 86627957, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

I2 was dissolved in a mixture of THF and H2O (4:1, 0.35M solution) at RT and LiOH.H2O (1.1 eq.) was added and the mixture was then stirred for 1.5 hr. 1M HCl was added until pH 4-5, then the THF was removed under reduced pressure. The aqueous phase was extracted with EtOAc (3×); the collected organic phases were washed with brine and then dried (Na2SO4). After removal of the solvent the title compound was obtained as a colorless oil which solidified upon standing, this was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ: 5.23 (1H, br. s), 4.13 (1H, br. s), 2.21 (2H, t, J=7.4 Hz), 1.75-1.90 (1H, m), 1.70-1.50 (3H, m), 1.45 (9H, s), 1.44 (9H, s), 1.50-1.25 (4H, m) MS (ES) C17H31NO6 requires: 345, found: 346 (M+H)+.

Workup

  1. customthe THF was removed under reduced pressure
  2. extractionThe aqueous phase was extracted with EtOAc (3×)
  3. washthe collected organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customAfter removal of the solvent the title compound
  6. customwas obtained as a colorless oil which
  7. customthis was used in the next step without purification

Sources & evidence

ORD record
ord-b61c438d72954f1bba822ee3043b9d8a
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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