Sodium Hydroxide → HCID 67441841, compound

HRID 1400938Notes

Reaction equation

HRID 1400938 reaction equation
[CH:1]1([NH:4][C:5](=[O:47])[NH:6][C:7]2[CH:45]=[CH:44][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]6[CH2:33][CH2:32][CH:31]([NH:34][C:35](=[O:43])[NH:36][CH2:37][C:38]([O:40]CC)=[O:39])[CH2:30][CH2:29]6)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:46])[CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:4][C:5](=[O:47])[NH:6][C:7]2[CH:45]=[CH:44][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]6[CH2:29][CH2:30][CH:31]([NH:34][C:35](=[O:43])[NH:36][CH2:37][C:38]([OH:40])=[O:39])[CH2:32][CH2:33]6)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:46])[CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442954HCID 67442954, compound

Product 1

HCID 67441841HCID 67441841, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 425 (78 mg, 0.12 mmol) in MeOH (3 mL) was added 1N NaOH (0.6 mL, 0.6 mmol). The reaction mixture was stirred at RT for 20 h. The reaction mixture was then concentrated, diluted with water and the pH was adjusted to 6-7 by addition of 1N HCl. To the resulting suspension was added MeOH to dissolve the mixture clearly, and purified via Biotage [KP-C18-HS 30 g, gradient 20-95% (methanol/water)]. Title compound 426 was obtained as a white solid (79.5 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): one H of carboxylic acid is missing, 10.17 (brs, 1H), 8.53 (d, J=1.6 Hz, 1H), 8.51 (d, J=5.2 Hz, 1H), 8.29 (s, 1H), 8.20 (d, J=8.0 Hz, 1H), 8.02 (brs, 1H), 7.81 (dd, J=8.0, 2.0 Hz, 1H), 7.76 (dd, J=14.0, 2.4 Hz, 1H), 7.33 (t, J=9.0 Hz, 1H), 7.28 (dd, J=9.2, 2.0 Hz, 1H), 6.65 (d, J=4.4 Hz, 1H), 6.25 (d, J=7.6 Hz, 1H), 5.59 (t, J=3.6 Hz, 1H), 4.15-4.09 (m, 1H), 3.51 (s, 2H), 3.28 (d, J=4.4 Hz, 2H), 2.72-2.65 (m, 2H), 2.58-2.51 (m, 1H), 2.11-2.02 (m, 2H), 1.76-1.66 (m, 2H), 1.38-1.25 (m, 2H), 0.63-0.56 (m, 2H), 0.44-0.38 (m, 2H). MS (m/z): 634.5 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with water
  3. additionthe pH was adjusted to 6-7 by addition of 1N HCl
  4. additionTo the resulting suspension was added MeOH
  5. dissolutionto dissolve the mixture clearly
  6. custompurified via Biotage [KP-C18-HS 30 g, gradient 20-95% (methanol/water)]

Sources & evidence

ORD record
ord-d99a662a1a8f43a5aa8f030dff5c1a5a
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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