Sodium Hydroxide → HCID 118318889, compound

HRID 921247Notes

Reaction equation

HRID 921247 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[N:35][C:34]2=[CH:38][C:31]3=[N:32][N:33]2[C:13]=1[N:14]1[CH2:41][CH2:40][C:17]([CH3:42])([O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([F:39])[CH:25]=[CH:26][C:27]=2[CH2:28][O:29][CH2:30]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:36]([CH3:37])=[N:35][C:34]2=[CH:38][C:31]3=[N:32][N:33]2[C:13]=1[N:14]1[CH2:15][CH2:16][C:17]([CH3:42])([O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([F:39])[CH:25]=[CH:26][C:27]=2[CH2:28][O:29][CH2:30]3)[CH2:40][CH2:41]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118318888HCID 118318888, compound

Product 1

HCID 118318889HCID 118318889, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (2S)-2-(tert-butoxy)-2-{16-fluoro-4,23-dimethyl-11,22-dioxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,13(18),14,16-heptaen-3-yl}acetate (32 mg, 0.055 mmol) and NaOH (2.196 mg, 0.055 mmol) in EtOH (2 mL) was refluxed for 2 h. It was then cooled to rt and purified by preparative HPLC to isolate (2S)-2-(tert-butoxy)-2-{16-fluoro-4,23-dimethyl-11,22-dioxa-1,5,7,8tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,13(18),14,16-heptaen-3-yl}acetic acid (13.9 mg, 0.025 mmol, 44.7% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.49-7.41 (m, 1H), 7.11-7.00 (m, 2H), 6.47 (s, 1H), 5.91 (s, 1H), 4.92 (d, J=11.7 Hz, 1H), 4.75 (d, J=12.1 Hz, 1H), 4.71-4.55 (m, 3H), 3.84 (t, J=10.6 Hz, 1H), 3.50 (m, 2H), 3.16-3.01 (m, 3H), 2.59 (d, J=11.7 Hz, 1H), 2.53 (s, 3H), 1.99-1.79 (m, 4H), 1.77-1.54 (m, 2H), 1.24 (s, 3H), 1.19 (s, 9H). LCMS (M+1)=555.2.

Workup

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

Sources & evidence

ORD record
ord-5eba50d12b6445b5998355e9a77ce98d
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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