Sodium Hydroxide → HCID 86710834, compound

HRID 1400781Notes

Reaction equation

HRID 1400781 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[N:39][C:38]2=[CH:42][C:35]3=[N:36][N:37]2[C:12]=1[N:13]1[CH2:47][CH2:46][C:16]([CH3:48])([O:17][CH2:18][CH:19]=[CH:20][CH2:21][C@H:22]([CH3:45])[O:23][C:24]2[CH:25]=[C:26]([CH3:44])[CH:27]=[CH:28][C:29]=2[C:30]2[CH:43]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[N:39][C:38]2=[CH:42][C:35]3=[N:36][N:37]2[C:12]=1[N:13]1[CH2:14][CH2:15][C:16]([CH3:48])([O:17][CH2:18][CH:19]=[CH:20][CH2:21][C@H:22]([CH3:45])[O:23][C:24]2[CH:25]=[C:26]([CH3:44])[CH:27]=[CH:28][C:29]=2[C:30]2[CH:43]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:46][CH2:47]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86710835HCID 86710835, compound

Product 1

HCID 86710834HCID 86710834, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl (2S)-2-(tert-butoxy)-2-[(22S)-4,18,22,28-tetramethyl-21,27-dioxa-1,5,7,8-tetraazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate (8 mg, 0.012 mmol), NaOH (0.061 mL, 0.061 mmol) in MeOH (1.5 mL) was refluxed for 3 h. It was then filtered and prep-HPLC to isolate 1.4 mg (18%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ 8.43 (s, 1H), 7.92 (d, J=7.9 Hz, 1H), 7.51 (t, J=7.6 Hz, 1H), 7.28 (d, J=7.6 Hz, 1H), 7.14 (d, J=7.6 Hz, 1H), 7.09 (s, 1H), 6.99 (s, 1H), 6.82 (d, J=7.3 Hz, 1H), 6.30 (br. s., 1H), 5.75-5.59 (m, 2H), 4.77 (t, J=11.6 Hz, 1H), 4.58 (br. s., 1H), 4.01-3.92 (m, 1H), 3.91-3.83 (m, 1H), 3.60-3.20 (m, 2H), 2.75 (d, J=7.3 Hz, 1H), 2.51 (s, 3H), 2.40-2.26 (m, 4H), 2.17 (br. s., 1H), 2.03 (d, J=13.7 Hz, 1H), 1.86 (d, J=12.5 Hz, 1H), 1.68-1.53 (m, 2H), 1.22 (s, 3H), 1.16 (s, 9H), 1.05 (d, J=6.1 Hz, 3H). LCMS (M+1)=639.3.

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationIt was then filtered

Sources & evidence

ORD record
ord-2512074ce4294bd6a5d2d42bc20d722c
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

Loading…