Potassium Hydroxide → HCID 19700441, compound

HRID 861855Notes

Reaction equation

HRID 861855 reaction equation
[CH3:1][N:2]([CH3:49])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[N:15]([C:24](=[O:41])[CH2:25][NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38]CC)=[O:37])[CH:31]=3)=[O:28])[CH:14]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[K+]>CO.O>[C:45]([O:44][C:42]([CH:14]1[CH2:13][CH:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:49])[CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[N:15]1[C:24](=[O:41])[CH2:25][NH:26][C:27](=[O:28])[NH:29][C:30]1[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=1)[C:36]([OH:38])=[O:37])=[O:43])([CH3:48])([CH3:46])[CH3:47]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86752038HCID 86752038, compound

Product 1

HCID 19700441HCID 19700441, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A The process is performed as described in Example 1A, but starting with 1.5 g of tert-butyl (2RS,4SR,5RS)-4-(4-dimethylaminophenyl)sulphonyl-1-{2-[3-(3-ethoxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-2-pyrrolidinecarboxylate and 0.12 g of potassium hydroxide in a mixture of 60 cm3 of methanol and 20 cm3 of distilled water. After treatment, 0.12 g of (2RS,4SR,5RS)-3-(3-{2-[2-tert-butoxycarbonyl-4-(4-dimethylaminophenyl)sulphonyl-5-(2-fluorophenyl)-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid is obtained [Rf=0.4; eluent: methylene chloride/methanol (90/10); 1H NMR spectrum (250 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 393 K, δ in ppm): 1.52 (s, 9H: C(CH3)3); 2.43 and 2.77 (2 mts, 1H each: CH2 at 3); 3.04 (s, 6H: N(CH3)2); 3.63 and 3.99 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 3.86 (mt, 1H: H4); 4.56 (broad t, J=8 Hz, 1H: H2); 5.71 (d, J=3 Hz, 1H: H5); 6.81 (d, J=8.5 Hz, 2H: H of the aromatic at 4 (H ortho to the N(CH3)2)); from 7.00 to 7.70 (mt, 6H: aromatic H); 7.68 (d, J=8.5 Hz, 2H: H of the aromatic at 4 (H meta to the N (CH3)2)); 7.80 (mt 1H: H of the aromatic at 5 (H6)); 8.00 (mt, 1H: aromatic H (H2: ortho to the COOH))].

Sources & evidence

ORD record
ord-1da1a55230944563970500c1111db9c9
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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