(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 70641235, compound

HRID 1630128Notes

Reaction equation

HRID 1630128 reaction equation
Cl.[CH2:2]([N:4]([CH2:17][CH3:18])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]([OH:16])=O)[CH2:8]1)=[O:6])[CH3:3].[NH2:19][C@@H:20]([CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)=[O:22]>>[CH2:40]([O:39][CH2:38][C@H:20]([NH:19][C:14](=[O:16])[CH2:13][N:9]1[CH2:10][CH2:11][CH2:12][CH:7]([C:5]([N:4]([CH2:2][CH3:3])[CH2:17][CH3:18])=[O:6])[CH2:8]1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)=[O:22])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 67009761HCID 67009761, compound

Product 1

HCID 70641235HCID 70641235, compoundYield 41.8%

Procedure

Proceeding as in Example 1, but substituting 2-(3-(diethylcarbamoyl)piperidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 231, 1-(2-((S)-3-(benzyloxy)-1-(4-(4-fluorophenoxy)phenylamino)-1-oxopropan-2-ylamino)-2-oxoethyl)-N,N-diethylpiperidine-3-carboxamide (20.2 mg, 41.8%). 1H-NMR (400 MHz, DMSO-D6): σ 10.22 (s, 1H), 8.01 (t, 1H), 7.61 (d, 2H), 7.27 (m, 6H), 7.00 (m, 4H), 4.70 (m, 1H), 4.52 (s, 2H), 3.71 (m, 2H), 3.27 (m, 4H), 3.02 (m, 6H), 2.15 (m, 2H), 1.63 (m, 3H), 1.35 (m, 1H), 1.06 (m, 3H), 0.93 (m, 3H). MS (EI) for C34H41FN4O5: 605.8 (MH+).

Sources & evidence

ORD record
ord-df5da27d319e4e138f107a4964e36d77
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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