(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009757, compound

HRID 1630108Notes

Reaction equation

HRID 1630108 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH:5]=[CH:4][CH2:3]1.[NH2:11][C@@H:12]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[O:14]>>[CH2:32]([O:31][CH2:30][C@H:12]([NH:11][C:8](=[O:10])[CH2:7][N:2]1[CH2:3][CH:4]=[CH:5][CH2:6]1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[O:14])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67010762HCID 67010762, compound

Product 1

HCID 67009757HCID 67009757, compoundYield 65.6%

Procedure

Proceeding as in Example 1, but substituting 2-(2,5-dihydro-1H-pyrrol-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 214, (S)-3-(benzyloxy)-2-(2-(2,5-dihydro-1H-pyrrol-1-yl)acetamido)-N-(4-(4-fluorophenoxy)phenyl)propanamide (25.7 mg, 65.6%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 7.96 (d, 1H), 7.60 (d, 2H), 7.27-7.32 (m, 5H), 7.21 (m, 2H), 6.98-7.04 (m, 4H), 4.72 (m, 1H), 4.52 (s, 2H), 3.69-3.74 (m, 2H), 3.30 (s, 2H), 3.13 (d, 1H), 2.56 (d, 2H), 1.72 (s, 1H). MS (EI) for C28H28FN3O4. found 490.5 (MH+).

Sources & evidence

ORD record
ord-09f85bd8580d4b8291b0401492ea6d68
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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