Hydrochloric Acid → HCID 91172680, compound

HRID 643064Notes

Reaction equation

HRID 643064 reaction equation
[CH2:1]([C@H:8]([NH:39]C(=O)OC(C)(C)C)[C@@H:9]([OH:38])[CH2:10][N:11]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[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>[NH2:39][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([OH:38])[CH2:10][N:11]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:30][CH:31]=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 90763427HCID 90763427, compound

Product 1

HCID 91172680HCID 91172680, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 7C (0/37 g, 0.59 mmol) in THF (4 mL) was treated with 4N HCl (1 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 and washed with brine, dried over sodium sulfate, filtered and the solvents were evaporated to give 0.28 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 brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents were evaporated

Sources & evidence

ORD record
ord-6f83bed50b564fc4ac262117b3abd79f
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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