Water → 3-[2(R)-Benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide

HRID 1080747Notes

Reaction equation

HRID 1080747 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C@H:16]([CH3:38])[CH2:17][NH:18][C:19]([CH3:37])([CH3:36])[CH2:20][C:21]([NH:23][C@@H:24]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[NH:26][C:25]1=[O:35])=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:8]([O:15][C@H:16]([CH3:38])[CH2:17][NH:18][C:19]([CH3:37])([CH3:36])[CH2:20][C:21]([NH:23][C@@H:24]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[NH:26][C:25]1=[O:35])=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 228679093-[2(R)-benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide trifluoroacetate

Product 1

HCID 186514253-[2(R)-Benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamideYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.03 g (3.788 mmol) of 3-[2(R)-benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide trifluoroacetate (Example 10, Step B) in 40 mL of methylene chloride was added 40 mL of water. The mixture was stirred vigorously while sufficient solid potassium carbonate was added to adjust the pH of the aqueous layer to 10-11. Stirring was discontinued and the layers allowed to separate. The organic layer was removed and the aqueous layer extracted twice more with methylene chloride. The combined extracts were dried over potassium carbonate, filtered and solvents removed under vacuum to afford 1.53 g (3.62 mmol, 95%) of the product as a white solid. 1H NMR (400 MHz, DMSO-d6): 1.04 (s, 3H), 1.06 (s, 3H), 1.14 (d, 7 Hz, 3H), 1.90 (m, 1H), 2.21 (m,3H), 2.60 (m,4H), 3.59 (m,1H), 4.23 (m,1H), 4.45 (d,10 Hz,1H),4.53 (d,10 Hz,1H),6.99 (d,8 Hz,1H), 7.12 (t,8 Hz,1H), 7.20-7.35 (m,7H), 8.72 (d,8 Hz,1H), 9.79 (s,1H).

Workup

  1. additionwas added
  2. customto separate
  3. customThe organic layer was removed
  4. extractionthe aqueous layer extracted twice more with methylene chloride
  5. dry with materialThe combined extracts were dried over potassium carbonate
  6. filtrationfiltered
  7. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-02731cdb02214cdfb0d9926be7f149d8
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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