Lithium Hydroxide → HCID 53633388, compound

HRID 2416745Notes

Reaction equation

HRID 2416745 reaction equation
[Li+].[OH-].[O:3]=[C:4]1[C@H:10]([CH2:11][C:12]([O:14]C)=[O:13])[CH2:9][C:8]2[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:19][C:7]=2[CH2:6][N:5]1[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.O>[O:3]=[C:4]1[C@H:10]([CH2:11][C:12]([OH:14])=[O:13])[CH2:9][C:8]2[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:19][C:7]=2[CH2:6][N:5]1[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 53994393HCID 53994393, compound

Product 1

HCID 53633388HCID 53633388, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 N LiOH (0.3 mL, 0.3 mmole) was added to a solution of methyl (S)-3-oxo-8-[3-(pyridin-2-ylamino)-1-propyloxy]-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (133 mg, 0.27 mmole) in THF (1.5 mL) and H2O (1.2 mL) at 0° C. The mixture was allowed to warm to RT over 18 hr. The mixture was washed with Et2O (2×5 mL) then a mild vacuum was applied to remove residual organic solvents. The aqueous layer was passed through a 0.45 μm Acrodisk filter, then was carefully acidified to pH 6 using 10% HCl in H2O at 0° C. The precipitate was collected, washed with H2O, and dried under vacuum at 50° C. to give the title compound as a white solid (62 mg, 48%): MS (ES) m/e 474 (M+H)+. Anal. Calcd for C28H31N3O4.0.75 H2O: C, 69.05; H, 6.75; N, 8.63. Found: C, 69.05; H, 6.66; N, 8.55.

Workup

  1. washThe mixture was washed with Et2O (2×5 mL)
  2. customto remove residual organic solvents
  3. filtrationfilter
  4. customat 0° C
  5. customThe precipitate was collected
  6. washwashed with H2O
  7. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-b80b8277ac0d4231bb80436ee8d72407
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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