Potassium Hydroxide → HCID 19700373, compound

HRID 861857Notes

Reaction equation

HRID 861857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[N:14]([C:23](=[O:40])[CH2:24][NH:25][C:26]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][C:36]([O:38]C)=[O:37])[CH:30]=3)=[O:27])[CH:13]([C:41](=[O:47])[NH:42]CC(C)C)[CH2:12]2)(=[O:10])=O)=[CH:4][CH:3]=1.[OH-:48].[K+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[N:14]([C:23](=[O:40])[CH2:24][NH:25][C:26](=[O:27])[NH:28][C:29]3[CH:30]=[C:31]([CH2:35][C:36]([OH:38])=[O:37])[CH:32]=[CH:33][CH:34]=3)[C:13]([C:41](=[O:47])[NH2:42])([CH2:15][CH:16]([CH3:21])[CH3:17])[CH2:12]2)(=[O:10])=[O:48])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19700414HCID 19700414, compound

Product 1

HCID 19700373HCID 19700373, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A The process is performed as in Example 1A, but starting with 3.35 g of (2 RS,4 SR,5RS)-4-(4-chlorophenyl)sulphonyl-5-(2-fluorophenyl)-2-isobutylcarbamoyl-1-{2-[3-(3-methoxycarbonylmethylphenyl)ureido]acetyl}-pyrrolidine and 0.36 g of potassium hydroxide in a mixture of 60 cm3 of methanol and 20 cm3 of distilled water. After treatment, 1.65 g of 3-(3-{2-[4-(4-chlorophenyl)sulphonyl-5-(2-fluorophenyl)-2-isobutyl carbamoyl-1-pyrrolidinyl]-2-oxoethyl}ureido)phenylacetic acid are obtained [Rf=0.45; 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 373 K, δ in ppm): 0.94 (d, J=6.5 Hz, 6H: C(CH3)2); 1.85 (mt, 1H: CH); from 2.30 to 2.55 and 2.84 (2 mts, 1H each: CH2 at 3); 3.06 (mt, 2H: NCH2); 3.50 (s, 2H: ArCH2COO); 3.67 and 3.88 (broad d and d respectively, J=17 Hz, 1H each:COCH2N); 4.08 (mt, 1H: H4); 4.78 (t, J=8 Hz, 1H: H2); 5.68 (d, J=3 Hz, 1H: H5); 6.12 (residual t:NHCO); 6.85 (broad d, J=7.5 Hz, 1H: aromatic H (H4 : ortho to the CH2)); from 6.95 to 7.30 (mt, 6H: aromatic H); 7.69 (broad d, J=8.5 Hz, 2H: H of the aromatic at 4 (H ortho to the Cl)); 7.96 (broad d, J=8.5 Hz, 2H: H aromatic at 4 (H meta to the Cl)); 8.20 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6)); 8.40 (residual s: CONHAr)].

Sources & evidence

ORD record
ord-57893606036d49cabac4551a4497e35c
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

Loading…