(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 67009520, compound

HRID 1630099Notes

Reaction equation

HRID 1630099 reaction equation
Cl.[N:2]1([CH2:8][C:9]([OH:11])=O)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[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:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]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])[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 670098402-(piperazin-1-yl)acetic acid hydrochloride

Product 1

HCID 67009520HCID 67009520, compoundYield 11%

Procedure

Proceeding as in Example 1, but substituting 2-piperazin-1-ylacetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 205, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(piperazin-1-yl)acetamido)propanamide (15 mg, 11%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.18 (br s, 1H), 7.97-7.95 (d, 1H), 7.61-7.57 (d, 2H), 7.33-7.27 (m, 5H), 7.23-7.19 (t, 2H), 7.04-6.97 (m, 4H), 4.71-4.69 (m, 1H), 4.52 (s, 2H), 3.78-3.67 (m, 2H), 2.96 (s, 2H), 2.77-2.75 (t, 4H), 2.42 (s, 4H), 1.91 (s, 1H). MS (EI) for C28H31FN4O4. found 507.0 (MH+).

Sources & evidence

ORD record
ord-3ad009442d7646a484dc346a8d8ef73f
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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