Lithium Hydroxide → HCID 18418862, compound

HRID 989637Notes

Reaction equation

HRID 989637 reaction equation
[Li+].[OH-].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]3[NH:22][CH:21]([CH2:23][C:24]([O:26]C)=[O:25])[C:20](=[O:28])[N:19]([CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:18][C:17]=3[CH:37]=2)=[O:12])=[CH:6][CH:5]=1>C1COCC1.O>[NH2:3][C:4]1[N:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]3[NH:22][CH:21]([CH2:23][C:24]([OH:26])=[O:25])[C:20](=[O:28])[N:19]([CH2:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:18][C:17]=3[CH:37]=2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86758534HCID 86758534, compound

Product 1

HCID 18418862HCID 18418862, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 N LiOH (1.1 mL, 1.1 mmol) was added dropwise to a mixture of methyl (±)-7-[[(6-amino-3-pyridinyl)amino]carbonyl]-3-oxo-4-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.23 g, 0.48 mmol) in THF (12 mL) and H2O (17 mL) at RT. After 22.5 h, the dark reddish-brown reaction mixture was concentrated on the rotavap to remove excess THF. The resulting reddish solution was cooled in an ice-bath, and neutralized with 1.0 N AcOH (1.8 mL). The precipitate was collected by suction filtration, washed with water and ether, and air-dried to give the title compound (0.19 g, 86%) as a pinkish-purple solid: 1H NMR (400 MHz, DMSO-d6) δ9.55 (s, 1H), 6.40-8.29 (m, 7H), 5.69 (s, 2H), 5.42 (d, J=17 Hz, 1H), 5.09 (br, 1H), 3.95 (dd, J=17,1H), 3.59-3.65 (m, 2H), 2.51-2.82 (m, 4H); MS (ES) m/e 460.2 (M+H)+. Anal. Calcd for C25H25N5O4.9/4 H2O: C, 60.05; H, 5.98; N, 14.01. Found: C, 59.79; H, 5.92; N, 13.64.

Workup

  1. concentrationthe dark reddish-brown reaction mixture was concentrated on the rotavap
  2. customto remove excess THF
  3. temperatureThe resulting reddish solution was cooled in an ice-bath
  4. filtrationThe precipitate was collected by suction filtration
  5. washwashed with water and ether
  6. customair-dried

Sources & evidence

ORD record
ord-e17f9b3174b64287ae5c50db9ce3f0a6
Source dataset
uspto-grants-2002_10
Patent number
US06458784B1

Reaction notes

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