Sodium Hydroxide → HCID 118318859, compound

HRID 921196Notes

Reaction equation

HRID 921196 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:39]([CH3:40])=[N:38][C:37]2=[CH:41][C:34]3=[N:35][N:36]2[C:13]=1[N:14]1[CH2:46][CH2:45][C:17]([CH3:47])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([CH3:44])[O:24][C:25]2[CH:26]=[C:27]([CH3:43])[CH:28]=[CH:29][C:30]=2[CH:31]([CH3:42])[O:32][CH2:33]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:39]([CH3:40])=[N:38][C:37]2=[CH:41][C:34]3=[N:35][N:36]2[C:13]=1[N:14]1[CH2:15][CH2:16][C:17]([CH3:47])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([CH3:44])[O:24][C:25]2[CH:26]=[C:27]([CH3:43])[CH:28]=[CH:29][C:30]=2[C@H:31]([CH3:42])[O:32][CH2:33]3)[CH2:45][CH2:46]1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118318851HCID 118318851, compound

Product 1

HCID 118318859HCID 118318859, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (2S)-2-(tert-butoxy)-2-[(20S)-4,12,16,20,26-pentamethyl-11,19,25-trioxa-1,5,7,8-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl]acetate (10 mg, 0.015 mmol) and sodium hydroxide (0.077 mL, 0.077 mmol) in EtOH (2 mL) was refluxed for 2 h. It was then cooled to rt and purified by preparative HPLC to isolate the first eluting isomer (2S)-2-(tert-butoxy)-2-[(12S,20S)-4,12,16,20,26pentamethyl-11,19,25-trioxa-1,5,7,8-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl]acetic acid (4.0 mg, 41.8%) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.24 (d, J=7.7 Hz, 1H), 6.82 (s, 1H), 6.74 (d, J=7.7 Hz, 1H), 6.31 (s, 1H), 5.56-5.43 (m, 2H), 4.63-4.39 (m, 4H), 3.66-3.51 (m, 4H), 2.85 (d, J=11.0 Hz, 1H), 2.48 (s, 3H), 2.28 (s, 3H), 1.94-1.86 (m, 2H), 1.75-1.48 (m, 8H), 1.28 (d, J=6.2 Hz, 3H), 1.19 (d, J=8.4 Hz, 6H), 1.14 (s, 9H). LCMS (M+1)=623.3.

Workup

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

Sources & evidence

ORD record
ord-03cc6e8f3b1b4c53bef46c23233cbb4c
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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