Sodium Hydroxide → HCID 118318879, compound

HRID 921232Notes

Reaction equation

HRID 921232 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[CH2:48][CH2:47][C:17]([CH3:49])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([CH3:46])[O:24][C:25]2[CH:26]=[C:27]([CH3:45])[CH:28]=[CH:29][C:30]=2[CH2:31][N:32]([CH:42]2[CH2:44][CH2:43]2)[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[CH2:48][CH2:47][C:17]([CH3:49])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([CH3:46])[O:24][C:25]2[CH:26]=[C:27]([CH3:45])[CH:28]=[CH:29][C:30]=2[CH2:31][N:32]([CH:42]2[CH2:43][CH2:44]2)[CH2:33]3)[CH2:16][CH2:15]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118318878HCID 118318878, compound

Product 1

HCID 118318879HCID 118318879, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (2S)-2-(tert-butoxy)-2-[(20S)-11-cyclopropyl-4,16,20,26-tetramethyl-19,25-dioxa-1,5,7,8,11-pentaazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl]acetate (70 mg, 0.104 mmol) and NaOH (0.311 mL, 0.311 mmol) in EtOH (2 mL) was refluxed for 2 h. It was then cooled to rt, purified by preparative HPLC to obtain (2S)-2-(tert-butoxy)-2-[(20S)-11-cyclopropyl-4,16,20,26-tetramethyl-19,25-dioxa-1,5,7,8,11-pentaazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl]acetic acid (42 mg, 0.065 mmol, 62.6% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.12 (d, J=7.3 Hz, 1H), 6.76 (s, 1H), 6.64 (d, J=7.7 Hz, 1H), 6.37 (s, 1H), 5.61 (s, 1H), 4.52 (br. s., 1H), 4.34 (t, J=12.3 Hz, 1H), 4.04 (d, J=14.3 Hz, 1H), 3.92 (d, J=15.0 Hz, 1H), 3.81 (d, J=14.3 Hz, 1H), 3.72 (d, J=15.0 Hz, 1H), 3.68-3.59 (m, 1H), 3.50-3.29 (m, 3H), 2.79-2.71 (m, 1H), 2.48 (s, 3H), 2.27 (s, 3H), 1.97 (br. s., 1H), 1.91 (s, 1H), 1.83 (d, J=12.8 Hz, 1H), 1.78-1.43 (m, 8H), 1.20 (d, J=5.9 Hz, 3H), 1.17 (s, 3H), 1.14 (s, 9H), 0.45 (d, J=5.5 Hz, 1H), 0.35 (d, J=4.8 Hz, 2H), 0.27 (br. s., 1H). LCMS (M+1)=648.5.

Workup

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

Sources & evidence

ORD record
ord-3ffe4721f51e47a7b673650628fefcf5
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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