4-Chloro-L-phenylalanine → 6-(5-((S)-2-Amino-3-(4-chlorophenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-one

HRID 2075411Notes

Reaction equation

HRID 2075411 reaction equation
F[C:2]1[CH:3]=[C:4]([C:11]2[S:15][C:14]([NH:16][C:17](=O)OC(C)(C)C)=[N:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[Cl:24][C:25]1[CH:45]=[CH:44][C:28]([CH2:29][C@H:30]2[CH2:34][O:33][S:32](=[O:36])(=[O:35])[N:31]2[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:27][CH:26]=1.N[C@@H](CC1C=CC(Cl)=CC=1)[C:48]([OH:50])=[O:49]>>[NH2:31][C@@H:30]([CH2:29][C:28]1[CH:27]=[CH:26][C:25]([Cl:24])=[CH:45][CH:44]=1)[CH2:17][NH:16][C:14]1[S:15][C:11]([C:4]2[CH:5]=[CH:6][C:7]3[NH:8][C:48](=[O:49])[O:50][C:2]=3[CH:3]=2)=[N:12][N:13]=1.[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][C@H:30]2[CH2:34][O:33][S:32](=[O:36])(=[O:35])[N:31]2[C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 7361904-Chloro-L-phenylalanineHCID 57991903tert-Butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamateHCID 86635689(S)-tert-Butyl 4-(4-chlorobenzyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Product 2

HCID 579919066-(5-((S)-2-Amino-3-(4-chlorophenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-oneHCID 86635689(S)-tert-Butyl 4-(4-chlorobenzyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Procedure

The title compound was synthesized in a similar manner to that described for Example 11, by alkylating tert-butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamate, prepared as in Example 1, with tert-butyl (4S)-4-(4-chlorobenzyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide instead of tert-butyl (4S)-4-(4-(trifluoromethyl)benzyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide. tert-Butyl (4S)-4-(4-chlorobenzyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide was prepared as shown in Scheme 1b but using (S)-2-amino-3-(4-chlorophenyl)propanoic acid instead of (S)-2-amino-3-(4-(trifluoromethyl)phenyl)propanoic acid. LCMS (API-ES) m/z: 402 (M+H+); 1H NMR (400 MHz, CD3OD): δ ppm 2.95-3.07 (m, 2H), 3.55-3.60 (m, 1H), 3.70-3.75 (m, 1H), 3.80-3.86 (m, 1H), 7.17 (d, J=8 Hz, 1H), 7.33 (d, J=8 Hz, 2H), 7.40 (d, J=8 Hz, 2H), 7.59 (d, J=8 Hz, 1H), 7.69 (s, 1H).

Sources & evidence

ORD record
ord-a74b970286214d898f47918554b440ec
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

Loading…