Hydrochloric Acid → HCID 91460602, compound

HRID 643072Notes

Reaction equation

HRID 643072 reaction equation
[CH2:1]([C@H:8]([NH:33]C(=O)OC(C)(C)C)[C@@H:9]([OH:32])[CH2:10][N:11]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:12][C:13](=[O:24])[C@@H:14]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C@@H:15]([CH3:18])[CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[NH2:33][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([OH:32])[CH2:10][N:11]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:12][C:13]([C@@H:14]([NH:19][C:20](=[O:21])[O:22][CH3:23])[C@@H:15]([CH3:18])[CH2:16][CH3:17])=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 91506378HCID 91506378, compound

Product 1

HCID 91460602HCID 91460602, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 26B (4.57 g, 8.2 mmol) in THF (60 mL) was treated with 4N HCl (14.4 mL). stirred at 60° C. for 3 hrs, and cooled to room temperature. The solvents were evaporated, and the crude residue was partitioned between ethyl acetate and 10% sodium bicarbonate. The organic layer was separated, washed with 10% sodium bicarbonate, brine, dried over sodium sulfate, filtered and the solvents were evaporated to give 3.41 g (89%) of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customThe solvents were evaporated
  3. customthe crude residue was partitioned between ethyl acetate and 10% sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with 10% sodium bicarbonate, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents were evaporated

Sources & evidence

ORD record
ord-5694aba173704bf79053e8c0837eef1b
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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