Lithium Hydroxide → HCID 9844289, compound

HRID 1601053Notes

Reaction equation

HRID 1601053 reaction equation
[Li+].[OH-].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]=1[CH2:12][NH:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]2[NH:25][CH:24]([CH2:26][C:27]([O:29]C)=[O:28])[C:23](=[O:31])[N:22]([CH3:32])[CH2:21][C:20]=2[CH:33]=1)=[O:15].CC#N.O>C1COCC1.O>[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]=1[CH2:12][NH:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]2[NH:25][CH:24]([CH2:26][C:27]([OH:29])=[O:28])[C:23](=[O:31])[N:22]([CH3:32])[CH2:21][C:20]=2[CH:33]=1)=[O:15]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 10788312HCID 10788312, compoundHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 9844289HCID 9844289, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 N LiOH (0.57 mL, 0.57 mmol) was added dropwise at RT to a mixture of methyl (±)-7-[[[(2-benzimidazolyl)methyl]amino]carbonyl]4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.11 g, 0.26 mmol) in THF (4 mL) and H2O (5 mL). The resulting light brownish-yellow solution was stirred for 21.5 h, then was concentrated on the rotavap. The resulting residue was lyophilized to give the crude product (0.11 g, 100%) as a yellowish powder. Preparative HPLC. (PRP-1® column, step gradient, 10-20% CH3CN/H2O-0.1% TFA) afforded the title compound: 1H NMR (250 MHz, DMSO-d6) δ 6.45-9.06 (m, 9H), 5.53 (d, J=16 Hz, 1H), 5.13 (m, 1H), 4.86 (d, J=5 Hz, 2H), 3.87 (d, J=17 Hz, 1H), 2.95 (s, 3H), 2.80 (dd, J=17, 9 Hz, 1H), 2.57 (dd, J=17, 5 Hz, 1H); MS (ES) m/e 408.2 (M+H)+. Anal. Calcd for C21H21N5O4.4/3 CF3CO2H.H2O: C, 49.22; H, 4.25; N, 12.13. Found: C, 49.24; H, 4.22; N, 12.11.

Workup

  1. concentrationwas concentrated on the rotavap
  2. customto give the crude product (0.11 g, 100%) as a yellowish powder

Sources & evidence

ORD record
ord-8bf5a8bd2e2f4cefb18409e843e9e439
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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