Sodium Hydroxide → HCID 66782728, compound

HRID 1095297Notes

Reaction equation

HRID 1095297 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([NH:35][S:36]([N:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[O:34])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([OH:25])([C:21]([O:23]C)=[O:22])[CH:18]([OH:26])[C:17]4[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([NH:35][S:36]([N:39]([CH3:40])[CH3:41])(=[O:37])=[O:38])=[O:34])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([OH:25])([C:21]([OH:23])=[O:22])[CH:18]([OH:26])[C:17]4[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66783044HCID 66783044, compound

Product 1

HCID 66782728HCID 66782728, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl rac-(5R,6S)-13-cyclohexyl-10-((((dimethylamino)sulfonyl)amino)carbonyl)-5,6-dihydroxy-3-(methyloxy)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carboxylate (57 mg, 0.10 mmol) in MeOH/THF (1:1, 2 mL) was added 1M NaOH aq. (0.5 mL). The reaction was sealed and heated at 80° C. for 20 min with microwave irradiation. The reaction was quenched with 1N HCl aq. (0.5 mL), diluted with H2O and concentrated to remove the organic solvents. The resulting precipitates were collected by filtration and dried under vacuum to yield rac-(5R,6S)-13-cyclohexyl-10-((((dimethylamino)sulfonyl)amino)carbonyl)-5,6-dihydroxy-3-(methyloxy)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carboxylic acid (42 mg, 0.074 mmol, 73%) as a yellow solid. 1HNMR (300 MHz, CD3OD) δ 0.73-2.20 (m, 10H), 2.92-3.05 (m, 1H), 3.02 (s, 6H), 3.54 (d, J=14.8 Hz, 1H), 3.93 (s, 3H), 4.71 (d, J=14.8 Hz, 1H), 4.94 (s, 1H), 7.05 (dd, J=8.4, 2.6 Hz, 1H), 7.40 (d, J=2.6 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.59 (dd, J=8.4, 1.5 Hz, 1H), 7.89 (d, J=8.4 Hz, 1H), 8.05 (d, J=1.5 Hz, 1H). LCMS: m/e 572 (M+H)+, ret time 3.34 min, column B, 4 minute gradient.

Workup

  1. customThe reaction was sealed
  2. customThe reaction was quenched with 1N HCl aq. (0.5 mL)
  3. additiondiluted with H2O
  4. concentrationconcentrated
  5. customto remove the organic solvents
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9079419cde164042b81ba040134d2b74
Source dataset
uspto-grants-2012_03
Patent number
US08138171B2

Reaction notes

Loading…