Water → HCID 21830457, compound

HRID 1601080Notes

Reaction equation

HRID 1601080 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][N:11]([CH3:31])[C:12]([C:14]1[CH:15]=[CH:16][C:17]2[NH:23][CH:22]([CH2:24][C:25]([O:27]C)=[O:26])[C:21](=[O:29])[NH:20][CH2:19][C:18]=2[CH:30]=1)=[O:13].O.[OH-].[Na+].FC(F)(F)C(O)=O>CO>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][N:11]([CH3:31])[C:12]([C:14]1[CH:15]=[CH:16][C:17]2[NH:23][CH:22]([CH2:24][C:25]([OH:27])=[O:26])[C:21](=[O:29])[NH:20][CH2:19][C:18]=2[CH:30]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57308363HCID 57308363, compound

Product 1

HCID 21830457HCID 21830457, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (±)-7-[[[(2-benzimidazolyl)methyl]methylamino]carbonyl]-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.040 g, 0.09 mmol) in a mixture of methanol (7.0 mL), water (0.7 mL), and 1.0 M NaOH (0.7 mL) was kept 16 h at RT. Trifluoroacetic acid (0.5 mL) was added and the solvents were removed to give the crude product. Purification by semi-preparative HPLC (YMC ODS-AQ, 15:85; acetonitrile:water, 0.1% TFA) gave the title compound: MS (ES) m/e 408.2 (M+H)+ ; 1H NMR (250 MHz, DMSO-d6) δ 8.19 (br t, J=4.5 Hz, 1H), 7.72 (m, 2H), 7.38 (m, 2H), 7.28 (d, J=8.4 Hz, 1H), 7.15 (s, 1H), 6.62 (d, J=8.4 Hz, 1H), 6.22 (br s, 1H), 5.05 (m, 1H), 4.95 (s, 2H), 3.74 (dd, 15.8, 7.4 Hz, 1H), 3.15 (s, 3H), 2.75 (dd, J=16.4, 8.5 Hz, 1H), 2.50 (m, 1H).

Workup

  1. customthe solvents were removed
  2. customto give the crude product
  3. customPurification by semi-preparative HPLC (YMC ODS-AQ, 15:85; acetonitrile:water, 0.1% TFA)

Sources & evidence

ORD record
ord-0b837385634c497082dca0efbdca05b2
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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