Methanol → HCID 67650775, compound
Reaction equation
C[O:2][C:3]([C@H:5]1[S:9][C@@H:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:7]([C:17](=[O:30])[CH2:18][NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=2)=[O:21])[C@H:6]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37])=[O:4].[OH-].[Na+].CO>O1CCCC1>[C:13]([O:12][C:10]([C@H:8]1[N:7]([C:17](=[O:30])[CH2:18][NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=2)=[O:21])[C@@H:6]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[C@H:5]([C:3]([OH:4])=[O:2])[S:9]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The process is performed in a similar manner to that described in Example 3, but starting with 0.35 g of tert-butyl (2S,4S,5S)-5-methoxycarbonyl-3-{2-[3-(3-methylphenyl)ureido]acetyl}-4-(2-fluorophenyl)-2-thiazolidinecarboxylate dissolved in 10 ml of tetrahydrofuran and 6.6 ml of aqueous 0.1N sodium hydroxide solution. 0.24 g of (2S,4S,5R)-2-tert-butoxycarbonyl-3-{2-[3-(3-methylphenyl)ureido]acetyl}-4-(2-fluorophenyl)-5-thiazolidinecarboxylic acid is thus obtained in the form of a white solid melting at 148° C., [α]D25 =-17°±1° (c=0.504; MeOH); 1H NMR (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 373 K, 5 in ppm): 1.51 (s, 9H: CH3 of the tert-butyl); 2.25 (s, 3H: ArCH3); 3.76 and 4.04 (broad d and d respectively, J=18 Hz, 1H each: COCH2N); 4.18 (d, J=3.5 Hz, 1H: H at C5 of the ring); 5.70 (s, 1H: H at C2 of the ring); 5.97 (d, J=3.5 Hz, 1H: H at C4 of the ring); 6.73 (broad d, J=7.5 Hz, 1H: aromatic H (H ortho to the CH3)); 7.06 (t, J=7.5 Hz, 1H: aromatic H (H meta to the CH3)); 7.10 to 7.50 (mt, 5H: aromatic H); 8.00 (mt, 1H: aromatic H at 6 (H meta to the F)).
Sources & evidence
- ORD record
- ord-6a1ac26d1d1d41a4995a5a0014b94834
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05686622
Reaction notes
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