HCID 86752039, compound → HCID 19700371, compound
Reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:46])[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]([CH3:38])(=[O:37])=[O:36])[CH2:25][CH:24]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[C:42]([O:41][C:39]([CH:24]1[CH2:25][CH:26]([S:35]([CH3:38])(=[O:36])=[O:37])[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:46])[NH:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:9]([OH:10])=[O:8])=[O:40])([CH3:45])([CH3:43])[CH3:44]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A The process is performed as in Example 2A, but starting with 3.4 g of tert-butyl (2RS,4SR,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-methylsulphonyl-2-pyrrolidinecarboxylate, 0.3 g of 10% palladium-on-charcoal and 100 cm3 of ethanol under a hydrogen atmosphere (130 kPa). After treatment, 2.4 g of (2RS,4SR,5RS)-3-(3-{2-[2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-methylsulphonyl-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 373 K, δ in ppm): 1.53 (s, 9H: C(CH3)3); from 2.45 to 2.88 (2 mts, 1H each: CH2 at 3); 3.10 (s, 3H: SO2CH3); 3.70 and 4.02 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 3.96 (mt, 1H: H4); 4.67 (t, J=8 Hz, 1H: H2); 5.83 (d, J=3 Hz, 1H: H5); from 7.10 to 7.65 (mt, 6H: aromatic H); 7.92 (broad t, J=8 Hz, 1H: H of the aromatic at 5 (H6)); 7.98 (t, J=1.5 Hz, 1H: aromatic H (H2 ortho to the COOH))].
Sources & evidence
- ORD record
- ord-d38f721b81c343969260756a0d9ab87e
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05716936
Reaction notes
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