HCID 86752033, compound → HCID 44213032, compound

HRID 861851Notes

Reaction equation

HRID 861851 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:53])[NH:19][CH2:20][C:21]([N:23]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[CH:26]([S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH3:45])[CH:39]=3)(=[O:37])=[O:36])[CH2:25][CH:24]2[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[C:49]([O:48][C:46]([CH:24]1[CH2:25][CH:26]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH3:45])[CH:39]=2)(=[O:37])=[O:36])[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[N:23]1[C:21](=[O:22])[CH2:20][NH:19][C:18](=[O:53])[NH:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:9]([OH:10])=[O:8])=[O:47])([CH3:52])([CH3:50])[CH3:51]

Participants

4

Reactant 1

HCID 86752033HCID 86752033, compound

Product 1

HCID 44213032HCID 44213032, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A The process is performed as described in Example 2A, but starting with 5.3 g of tert-butyl (2RS,4SR,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(3-methoxyphenyl)sulphonyl-2-pyrrolidinecarboxylate, 0.4 g of 10% palladium-on-charcoal and 100 cm3 of ethanol under a hydrogen atmosphere (130 kPa). After treatment, 3.5 g of (2RS,4SR,5RS)-3-(3-{2-[2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-(3-methoxyphenyl)sulphonyl-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid are obtained [Rf=0.3; 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): 1.54 (s, 9H: C(CH3)3); from 2.40 to 2.60 and 2.82 (2 mts, 1H each: CH2 at 3); 3.68 and 3.98 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 3.88 (s, 3H: OCH3); 4.11 (mt, 1H: H4); 4.67 (t, J=8 Hz, 1H: H2); 5.72 (d, J=3 Hz, 1H: H5); from 7.00 to 7.65 (mt, 10H: aromatic H); 7.80 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6)); 8.00 (mt, 1H: aromatic H (H2: ortho to the COOH))].

Sources & evidence

ORD record
ord-4383382f6d664ecabb7ff4d92c1f72bc
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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