Sodium Hydroxide → HCID 118318876, compound

HRID 921227Notes

Reaction equation

HRID 921227 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][CH2:22][C:23]2[CH:39]=[C:27]([CH2:28][O:29][CH2:30]3)[CH:26]=[CH:25][CH:24]=2)[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][CH2:22][C:23]2[CH:39]=[C:27]([CH2:28][O:29][CH2:30]3)[CH:26]=[CH:25][CH:24]=2)[CH2:40][CH2:41]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118318874HCID 118318874, compound

Product 1

HCID 118318876HCID 118318876, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (2S)-2-(tert-butoxy)-2-{4,23-dimethyl-11,22-dioxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.113,17.02,7]nonacosa-2,4,6(29),8,13(28),14,16-heptaen-3-yl}acetate (20 mg, 0.035 mmol) and NaOH (0.035 mL, 0.035 mmol) in EtOH (2 mL) was refluxed for 2 h. It was then cooled to rt, filtered and purified by preparative HPLC to obtain (2S)-2-(tert-butoxy)-2-{4,23-dimethyl-11,22-dioxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.113,17.02,7]nonacosa-2,4,6(29),8,13(28),14,16-heptaen-3-yl}acetic acid (17 mg, 0.031 mmol, 89% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.41 (s, 1H), 7.33-7.24 (m, 1H), 7.16 (d, J=7.0 Hz, 2H), 6.51 (s, 1H), 5.64 (s, 1H), 4.50-4.29 (m, 5H), 3.65-3.58 (m, 1H), 3.57-3.38 (m, 3H), 2.76 (d, J=11.4 Hz, 1H), 2.51 (s, 3H), 2.66 (t, J=8.1 Hz, 2H), 1.97 (d, J=13.6 Hz, 1H), 1.89-1.51 (m, 7H), 1.22 (s, 3H), 1.15 (s, 9H). LCMS (M+1)=551.6.

Workup

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

Sources & evidence

ORD record
ord-a42467adb15a447aac15b093963d8cc4
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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