Sodium Hydroxide → HCID 118318866, compound

HRID 921217Notes

Reaction equation

HRID 921217 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:38]([CH3:39])=[N:37][C:36]2=[CH:40][C:33]3=[N:34][N:35]2[C:13]=1[N:14]1[CH2:43][CH2:42][C:17]([CH3:44])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[C:26]([F:41])[CH:27]=[CH:28][C:29]=2[CH2:30][O:31][CH2:32]3)[CH2:16][CH2:15]1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:38]([CH3:39])=[N:37][C:36]2=[CH:40][C:33]3=[N:34][N:35]2[C:13]=1[N:14]1[CH2:15][CH2:16][C:17]([CH3:44])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[C:26]([F:41])[CH:27]=[CH:28][C:29]=2[CH2:30][O:31][CH2:32]3)[CH2:42][CH2:43]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118318865HCID 118318865, compound

Product 1

HCID 118318866HCID 118318866, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (2S)-2-(tert-butoxy)-2-{16-fluoro-4,25-dimethyl-11,24-dioxa-1,5,7,8-tetraazapentacyclo[23.2.2.16,9.02,7.013,18]triaconta-2,4,6(30),8,13(18),14,16-heptaen-3-yl}acetate (36 mg, 0.059 mmol) and NaOH (0.295 mL, 0.295 mmol) in EtOH (2 mL) was refluxed for 2 h. It was then filtered and purified by preparative HPLC to obtain (2S)-2-(tert-butoxy)-2-{16-fluoro-4,25-dimethyl-11,24-dioxa-1,5,7,8-tetraazapentacyclo[23.2.2.16,9.02,7.013,18]triaconta-2,4,6(30),8,13(18),14,16-heptaen-3-yl}acetic acid (23.3 mg, 0.040 mmol, 67.8% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.37-7.29 (m, 1H), 7.04 (d, J=9.9 Hz, 1H), 6.95 (t, J=8.3 Hz, 1H), 6.49 (s, 1H), 5.59 (s, 1H), 4.72-4.66 (m, 1H), 4.65-4.57 (m, 3H), 4.45 (t, J=11.7 Hz, 1H), 3.58-3.30 (m, 4H), 2.84-2.75 (m, 1H), 2.66 (d, J=12.8 Hz, 2H), 2.50 (br. s., 3H), 1.93-1.88 (m, 1H), 1.83 (d, J=13.9 Hz, 1H), 1.70-1.49 (m, 8H), 1.19 (s, 3H), 1.14 (s, 9H). LCMS (M+1)=583.7.

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationIt was then filtered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-62973b23a342433290bf266ef9281d02
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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