Sodium Hydroxide → HCID 178462263, compound

HRID 27813Notes

Reaction equation

HRID 27813 reaction equation
[N:1]1([C:80]([O:82][CH2:83][C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=2)=[O:81])[CH2:79][CH2:78][CH2:77][C@H:2]1[C:3]([NH:5][C@H:6]([C:17]([NH:19][C@H:20]([C:36]([NH:38][C@H:39]([C:50]([NH:52][C@H:53]([C:69]([NH:71][CH2:72][C:73]([O:75]C)=[O:74])=[O:70])[CH2:54][CH2:55][CH2:56][CH2:57][NH:58][C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])=[O:51])[C@@H:40]([CH3:49])[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:37])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:18])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:16])[NH:12][N+:13]([O-:15])=[O:14])=[O:4].[OH-].[Na+]>CN(C=O)C.CO>[N:1]1([C:80]([O:82][CH2:83][C:84]2[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=2)=[O:81])[CH2:79][CH2:78][CH2:77][C@H:2]1[C:3]([NH:5][C@H:6]([C:17]([NH:19][C@H:20]([C:36]([NH:38][C@H:39]([C:50]([NH:52][C@H:53]([C:69]([NH:71][CH2:72][C:73]([OH:75])=[O:74])=[O:70])[CH2:54][CH2:55][CH2:56][CH2:57][NH:58][C:59]([O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:60])=[O:51])[C@@H:40]([CH3:49])[O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:37])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])=[O:18])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:16])[NH:12][N+:13]([O-:15])=[O:14])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501689HCID 178501689, compound

Product 1

HCID 178462263HCID 178462263, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

A solution of compound (i) (0.87 g, 0.0007 M) in 50% DMF/methanol (30 ml) was treated with 1 N NaOH solution (1.7 ml) and stirred at R.T. for 2 hours. Acidification precipitated the product (0.43 g) in 50% yield. T.L.C. 2:1 CHCl3 :MeOH (I2 stain) showed one spot at Rf 0.77. [α]D25° =-4.1° (C=1, AcOH). The NMR was consistent with structure.

Workup

  1. customAcidification precipitated the product (0.43 g) in 50% yield
  2. custom[α]D25° =-4.1° (C=1, AcOH)

Sources & evidence

ORD record
ord-29704118d0294beeb5196fa574f4a917
Source dataset
uspto-grants-1980_09
Patent number
US04223016

Reaction notes

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