(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 45376362, compound

HRID 1630105Notes

Reaction equation

HRID 1630105 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([OH:15])=O.[NH2:16][C@@H:17]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19]>>[CH2:37]([O:36][CH2:35][C@H:17]([NH:16][C:13](=[O:15])[CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([F:2])[CH:4]=2)[NH:8][CH:7]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67009458HCID 67009458, compound

Product 1

HCID 45376362HCID 45376362, compoundYield 70%

Procedure

Proceeding as in Example 1, but substituting 2-(5-fluoro-1H-indol-3-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 212, (S)-3-(benzyloxy)-2-(2-(5-fluoro-1H-indol-3-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (78 mg, 70%). 1H-NMR (400 MHz, DMSO-D6): σ 10.98 (s, 1H), 10.17 (s, 1H), 8.37 (d, 1H), 7.63-7.57 (m, 2H), 7.39-7.16 (m, 9H), 7.05-6.95 (m, 4H), 6.93-6.86 (m, 1H), 4.75-4.67 (m, 1H), 4.50 (s, 2H), 3.70-3.53 (m, 4H). MS (EI) for C32H27F2N3O4. found 555.9 (MH+).

Sources & evidence

ORD record
ord-3f109cd43c2e4d1aa84da030df9a968d
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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