Potassium Hydroxide → HCID 19700381, compound

HRID 861860Notes

Reaction equation

HRID 861860 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:47])[NH:14][CH2:15][C:16]([N:18]2[CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[CH:21]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH2:20][CH:19]2[C:40](=[O:46])[NH:41][CH2:42][CH:43]([CH3:45])[CH3:44])=[O:17])[CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[K+]>CO.O>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH:22]1[N:18]([C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:47])[NH:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:4]([OH:5])=[O:3])[CH:19]([C:40](=[O:46])[NH:41][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:20][CH:21]1[S:30]([C:33]1[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=1)(=[O:31])=[O:32]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67661912HCID 67661912, compound

Product 1

HCID 19700381HCID 19700381, compoundYield 6.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A The process is performed as described in Example 1A, but starting with 3 g of (2RS,4SR,5RS)-1-{2-[3-(3-ethoxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-2-isobutylcarbamoyl-4-(4-methylphenyl)sulphonylpyrrolidine and 0.252 g of potassium hydroxide in a mixture of 80 cm3 of methanol and 20 cm3 of distilled water. After treatment, 0.18 g of (2RS,4SR,5RS)-3-(3-{2-[5-(2-fluorophenyl)-2-isobutylcarbamoyl-4-(4-methylphenyl)sulphonyl-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid is obtained [Rf=0.6; 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 393 K, δ in ppm): 0.96 (d, J=6.5 Hz, 6H: C(CH3)2); 1.85 (mt, 1H: CH); from 2.30 to 2.55 and 2.82 (2 mts, 1H each: CH2 at 3); 2.48 (s, 3H: CH3); 3.07 (mt, 2H: NCH2); from 3.60 to 3.80 and 3.88 (mt and d respectively, J=17 Hz), 1H each: COCH2N); 4.00 (mt, 1H: H4); 4.78 (t, J=7 Hz, 1H: H2); 5.71 (very broad s, 1H: H5); from 6.95 to 7.65 (mt, 6H: aromatic H); 7.49 (d, J=7.5 Hz, 2H: H of the aromatic at 4 (H ortho to the CH3)); 7.86 (d, J=7.5 Hz, 2H: H of the aromatic at 4 (H meta to the CH3)); 8.02 (mt, 1H: aromatic H (H2: ortho to the COOH)); 8.22 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6))].

Sources & evidence

ORD record
ord-dde97591785f4f2bbe41a42d847cc11d
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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