2-(Morpholin-4-yl)acetic acid hydrochloride → (S)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-morpholinoacetamido)propanamide

HRID 1630103Notes

Reaction equation

HRID 1630103 reaction equation
Cl.[N:2]1([CH2:8][C:9]([OH:11])=O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[NH2:12][C@@H:13]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[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]>>[F:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][O:32][CH2:31][C@H:13]([NH:12][C:9](=[O:11])[CH2:8][N:2]2[CH2:3][CH2:4][O:5][CH2:6][CH2:7]2)[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)=[O:15])=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 177509462-(Morpholin-4-yl)acetic acid hydrochlorideHCID 67009398(S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 67009194(S)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-morpholinoacetamido)propanamideYield 55%

Procedure

Proceeding as in Example 1, but substituting 2-morpholin-4-ylacetic acid hydrochloride and (S)-2-amino-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 210, (S)-3-(4-fluorobenzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-morpholinoacetamido)propanamide (60 mg, 55%). 1H-NMR (400 MHz, CDCl3): δ 8.45 (s, 1H), 8.00 (s, 1H), 7.37-7.25 (m, 5H), 7.10-6.90 (m, 7H), 4.79-4.73 (m, 1H), 4.63 (m, 2H), 4.00-3.80 (m, 6H), 3.20-3.10 (s, 2H), 2.60-2.45 (m, 4H). MS (EI) for C28H29F2N3O5 found 526 (MH+).

Sources & evidence

ORD record
ord-ff492fbabbb54b9d8cfd118094ecbc87
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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