Sodium Hydroxide → HCID 86751594, compound

HRID 2293791Notes

Reaction equation

HRID 2293791 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]([C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:47])[NH:21][CH2:22][C:23]([N:25]2[C@@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@@H:28]([C:36]([O:38]C)=[O:37])[S:27][C@H:26]2[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:24])[CH:16]=[CH:17][CH:18]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([C@H:11]([C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:47])[NH:21][CH2:22][C:23]([N:25]2[C@@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:28]([C:36]([OH:38])=[O:37])[S:27][C@H:26]2[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:24])[CH:16]=[CH:17][CH:18]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86751595HCID 86751595, compound

Product 1

HCID 86751594HCID 86751594, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The process is performed as in Example 3, but starting with 0.3 g of methyl (2S,4S,5S)-3-{2-{3-[(S)-3-(1-benzyloxycarbonylethyl)phenyl]ureido}acetyl}-2-tert-butoxycarbonyl-4-phenyl-5-thiazolidinecarboxylate and 4.5 ml of aqueous 0.1N sodium hydroxide solution. 0.15 g of (2S,4S,5R)-3-{2-{3-[(S)-3-(1-benzyloxycarbonylethyl)phenyl]ureido}acetyl}-2-tert-butoxycarbonyl-4-phenyl-5-thiazolidinecarboxylic acid is thus obtained in the form of a white solid melting at 96° C., [α]D25 =+6°±1° (c=0.46; MeOH); 1H NMR (250 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 393 K, δ in ppm): 1.45 (d, J=7.5 Hz, 3H: CH3); 1.51 (s, 9H: CH3 of the tert-butyl); 3.66 and 4.05 (broad d and d respectively, J=17.5 Hz, 1H each: COCH2N); 3.77 (q, J=7.5 Hz, 1H: CHCOO); 4.19 (d, J=4 Hz, 1H: H at C5 of the ring); 5.12 (s, 2H: OCH2); 5.71 (s, 1H: H at C2 of the ring); 5.77 (d, J=4 Hz, 1H: H at C4 of the ring); 6.85 (broad d, J=7.5 Hz, 1H: aromatic H (H ortho to the CH)); 7.15 (t, J=7.5 Hz, 1H: aromatic H (meta to the CH); from 7.20 to 7.50 (mt, 10H: aromatic H); 7.72 (broad d, J=7.5 Hz, 2H: H ortho to the phenyl at position 4).

Sources & evidence

ORD record
ord-2d5b12d5b562455182caac3d2f1eca61
Source dataset
uspto-grants-1997_11
Patent number
US05686622

Reaction notes

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