HCID 86752037, compound → HCID 19700432, compound

HRID 861854Notes

Reaction equation

HRID 861854 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:17]([C:26](=[O:48])[CH2:27][NH:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([O:40]CC4C=CC=CC=4)=[O:39])[CH:33]=3)=[O:30])[CH:16]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:17]([C:26](=[O:48])[CH2:27][NH:28][C:29](=[O:30])[NH:31][C:32]3[CH:33]=[C:34]([CH:35]=[CH:36][CH:37]=3)[C:38]([OH:40])=[O:39])[CH:16]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86752037HCID 86752037, compound

Product 1

HCID 19700432HCID 19700432, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The process is performed as described in Example 2A, but starting with 1.6 g of tert-butyl (2RS,4SR,5RS)-4-(4-acetamidophenyl)sulphonyl-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-2-pyrrolidinecarboxylate, 0.2 g of 10% palladium-on-charcoal and 100 cm3 of ethanol under a hydrogen atmosphere (130 kPa). After treatment, 0.9 g of (2RS,4SR,5RS)-3-(3-{2-[4-(4-acetamidophenyl)sulphonyl-2-tert-butoxycarbonyl-5-(2-fluorophenyl)-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid is obtained [Rf=0.3; eluent: methylene chloride/methanol (90/10); 1H NMR spectrum (300 MHz, (CD3)2SO, at a temperature of 393 K, δ in ppm): 1.55 (s, 9H: C(CH3)3); 2.12 (s, 3H: COCH3); 2.44 and 2.79 (2 mts, 1H each: CH2 at 3); 3.68 and 3.99 (mt and dd respectively (J=17 and 4.5 Hz), 1H each: COCH2N); 4.03 (mt, 1H: H4); 4.65 (broad t, J=7 Hz, 1H: H2); 5,72 (d, J=3 Hz, 1H: H5); 6.20 (t, J=4.5 Hz, 1H: NHCO); from 7.05 to 7.65 (mt, 6H: aromatic H); 7.80 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6)); 7.88 (limiting AB, J=7.5 Hz, 4H: H of the aromatic at 4); 8.00 (mt, 1H: aromatic H (H2: ortho to the COOH)); 8.65 (s, 1H: CONHAr); 10.03 (s, 1H: ArNH)].

Sources & evidence

ORD record
ord-a3f8fa2ef17b4323ace40e5af2f3a77d
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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