(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009827, compound

HRID 1630131Notes

Reaction equation

HRID 1630131 reaction equation
Cl.[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]([OH:11])=O.[NH2:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15]>>[CH2:33]([O:32][CH2:31][C@H:13]([NH:12][C:9](=[O:11])[CH2:8][N:4]1[CH2:5][CH2:6][CH2:7][CH:3]1[CH3:2])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)=[O:15])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 670107861222197-40-1

Product 1

HCID 67009827HCID 67009827, compoundYield 47%

Procedure

Proceeding as in Example 1, but substituting 2-(2-methylpyrrolidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 63, (2S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(2-methylpyrrolidin-1-yl)acetamido)propanamide (19 mg, 47%). 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 7.93 (t, 1H), 7.60 (d, 2H), 7.29 (m, 5H), 7.19 (m, 2H), 7.00 (m, 4H), 4.73 (s, 1H), 4.52 (s, 2H), 3.69 (m, 2H), 3.05 (m, 1H), 2.82 (m, 1H), 2.46 (m, 1H), 2.23 (m, 1H), 1.91 (m, 1H), 1.67 (m, 2H), 1.33 (m, 1H), 1.03 (d, 3H). MS (EI) for C29H32FN3O4: 506.5 (MH+).

Sources & evidence

ORD record
ord-53f8ae99b6f24b6db6834bef4e3542e1
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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