Potassium Hydroxide → HCID 19700434, compound

HRID 861861Notes

Reaction equation

HRID 861861 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:12]([C:13](=[O:29])[CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27]C)=[O:26])[CH:20]=2)=[O:17])[CH:11]([C:30](=[O:36])[NH:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:10][CH:9]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=1)(=[O:39])=[O:38].[OH-].[K+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:12]([C:13](=[O:29])[CH2:14][NH:15][C:16](=[O:17])[NH:18][C:19]2[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=2)[C:25]([OH:27])=[O:26])[CH:11]([C:30](=[O:36])[NH:31][CH2:32][CH:33]([CH3:34])[CH3:35])[CH2:10][CH:9]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=1)(=[O:38])=[O:39]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67661701HCID 67661701, compound

Product 1

HCID 19700434HCID 19700434, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A The process is performed as described in Example 1A, but starting with 2 g of (2RS,4SR,5RS)-5-(2-fluorophenyl)-2-isobutylcarbamoyl-1-{2-[3-(3-methoxycarbonylphenyl)ureido]acetyl}-4-(4-nitrophenyl)sulphonylpyrrolidine and 0.16 g of potassium hydroxide in a mixture of 60 cm3 of methanol and 20 cm3 of distilled water. After treatment, 0.9 g of (2RS,4SR,5RS)-3-(3-{2-[5-(2-fluorophenyl)-2-isobutylcarbamoyl-4-(4-nitrophenyl)sulphonyl-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid is obtained [Rf=0.2; eluent: methylene chloride/methanol (90/10); 1H NMR spectrum (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 383 K, δ in ppm): 0.94 (d, J=6.5 Hz, 6H: C(CH3)2); 1.89 (mt, 1H: CH); from 2.65 to 3.00 (2 mts, 1H each: CH2 at 3); 3.08 (mt, 2H: NCH2); 3.72 and 3.91 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 4.21 (mt, 1H: H4); 4.83 (t, J=7.5 Hz, 1H: H2); 5.71 (d, J=3 Hz, 1H: H5); from 6.95 to 7.65 (mt, 6H:aromatic H); 8.02 (mt, 1H: aromatic H (H2: ortho to the COOH)); 8.18 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6)); 8.25 (d, J=8.5 Hz, 2H: H of the aromatic at 4 (H meta to the NO2)); 8.42 (d, J=8.5 Hz, 2H: H of the aromatic at 4 (H ortho to the NO2))].

Sources & evidence

ORD record
ord-8e565443b1d74cf7a9150594e846844c
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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