HCID 19700438, compound → HCID 19700445, compound

HRID 861858Notes

Reaction equation

HRID 861858 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:52])[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]=[CH:40][C:39]=3[F:44])(=[O:37])=[O:36])[CH2:25][CH:24]2[C:45](=[O:51])[NH:46][CH2:47][CH:48]([CH3:50])[CH3:49])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[F:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH:27]1[N:23]([C:21](=[O:22])[CH2:20][NH:19][C:18](=[O:52])[NH:17][C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[C:9]([OH:10])=[O:8])[CH:24]([C:45](=[O:51])[NH:46][CH2:47][CH:48]([CH3:50])[CH3:49])[CH2:25][CH:26]1[S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[F:44])(=[O:37])=[O:36]

Participants

4

Reactant 1

HCID 19700438HCID 19700438, compound

Product 1

HCID 19700445HCID 19700445, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A The process is performed as described in Example 2A, but starting with 3.2 g of (2RS,4SR,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(2-fluorophenyl)sulphonyl-2-isobutylcarbamoylpyrrolidine, 0.35 g of 10% palladium-on-charcoal and 100 cm3 of ethanol under a hydrogen atmosphere (130 kPa). After treatment, 2.3 g of (2RS,4SR,5RS)-3-(3-{2-[5-(2-fluorophenyl)-4-(2-fluorophenyl)sulphonyl-2-isobutylcarbamoyl-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid are obtained [Rf=0.3; 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 83 K, δ in ppm): 0.96 (d, J=6.5 Hz, 6H: C(CH3)2); 1.88 (mt, 1H: CH); from 2.45 to 2.65 and 2.90 (2 mts, 1H each: CH2 at 3); 3.09 (mt, 2H: NCH2); 3.70 and 3.90 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 4.14 (mt, 1H: H4); 4.86 (t, J=8 Hz, 1H: H2); 5.70 (d, J=3 Hz, 1H: H5); from 6.90 to 8.00 (mt, 10H: aromatic H); 8.00 (mt, 1H: aromatic H (H2: ortho to the COOH)); 8.20 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6))].

Sources & evidence

ORD record
ord-fcd849efbce6424781f76c109f6946bf
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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