Sodium Hydroxide → HCID 118318882, compound

HRID 921237Notes

Reaction equation

HRID 921237 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:37]([CH3:38])=[N:36][C:35]2=[CH:39][C:32]3=[N:33][N:34]2[C:13]=1[N:14]1[CH2:42][CH2:41][C:17]([CH3:43])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[C:25]([CH3:40])[CH:26]=[CH:27][C:28]=2[CH2:29][O:30][CH2:31]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:37]([CH3:38])=[N:36][C:35]2=[CH:39][C:32]3=[N:33][N:34]2[C:13]=1[N:14]1[CH2:15][CH2:16][C:17]([CH3:43])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[C:25]([CH3:40])[CH:26]=[CH:27][C:28]=2[CH2:29][O:30][CH2:31]3)[CH2:41][CH2:42]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118318880HCID 118318880, compound

Product 1

HCID 118318882HCID 118318882, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (2S)-2-(tert-butoxy)-2-{4,16,24-trimethyl-11,23-dioxa-1,5,7,8-tetraazapentacyclo[22.2.2.16,9.02,7.013,18]nonacosa-2,4,6(29),8,13(18),14,16-heptaen-3-yl}acetate (30 mg, 0.051 mmol) and NaOH (0.152 mL, 0.152 mmol) in EtOH (2 mL) was refluxed for 2 h. It was then cooled to rt and purified by preparative HPLC to obtain (2S)-2-(tert-butoxy)-2-{4,16,24-trimethyl-11,23-dioxa-1,5,7,8-tetraazapentacyclo[22.2.2.16,9.02,7.013,18]nonacosa-2,4,6(29),8,13(18),14,16-heptaen-3-yl}acetic acid (24 mg, 0.042 mmol, 84% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.25 (d, J=7.3 Hz, 1H), 7.03-6.96 (m, 2H), 6.49 (s, 1H), 5.76 (br. s., 1H), 4.87-4.76 (m, 2H), 4.72 (d, J=12.1 Hz, 1H), 4.58 (d, J=12.1 Hz, 1H), 4.54-4.46 (m, 1H), 3.66-3.58 (m, 2H), 3.39 (m, 1H), 3.12 (br. s., 1H), 2.69-2.60 (m, 2H), 2.55 (br. s., 4H), 2.27 (s, 3H), 1.92-1.50 (m, 8H), 1.18 (s, 3H), 1.15 (s, 9H). LCMS (M+1)=565.4.

Workup

  1. temperaturewas refluxed for 2 h
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-47a2e930d1cd406f8b35c9116c0c3536
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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