Sodium Hydroxide → HCID 131711892, compound

HRID 27812Notes

Reaction equation

HRID 27812 reaction equation
[NH:1]([C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])[C@H:2]([C:18]([NH:20][C@H:21]([C:32]([NH:34][C@H:35]([C:51]([NH:53][CH2:54][C:55]([O:57]C)=[O:56])=[O:52])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])=[O:33])[C@@H:22]([CH3:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[OH-].[Na+]>CN(C=O)C.CO>[NH:1]([C:59]([O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:60])[C@H:2]([C:18]([NH:20][C@H:21]([C:32]([NH:34][C@H:35]([C:51]([NH:53][CH2:54][C:55]([OH:57])=[O:56])=[O:52])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42])=[O:33])[C@@H:22]([CH3:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131711893HCID 131711893, compound

Product 1

HCID 131711892HCID 131711892, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

A solution of compound (v) (0.92 g, 0.001 M) in 50% DMF/methanol was treated with 1 N NaOH solution (2.5 ml) and stirred at R.T. for 1 hour. Upon acidification the precipitated product (0.45 g) was recrystallised from methanol in 49% yield. M.P. 171°-173°. T.L.C. 2:1 CHCl3 :MeOH (t.butyl chloroformate/NaI-starch spray) showed one spot at Rf 0.50 [α]D25° =-5.4° (C=1, AcOH). The F.T. 13C NMR was consistent with structure.

Workup

  1. customUpon acidification the precipitated product (0.45 g) was recrystallised from methanol in 49% yield
  2. customat Rf 0.50 [α]D25° =-5.4° (C=1, AcOH)

Sources & evidence

ORD record
ord-915587692bcc455aafde4ab8085d6f99
Source dataset
uspto-grants-1980_09
Patent number
US04223016

Reaction notes

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