(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide → HCID 86659467, compound

HRID 1630115Notes

Reaction equation

HRID 1630115 reaction equation
Cl.[CH2:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][C:13]([OH:15])=O)[CH2:8][CH2:7]2)[CH2:5][O:4][O:3]1.[NH2:16][C@@H:17]([CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[O:19]>>[CH2:5]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:12][C:13]([NH:16][C@@H:17]([CH2:35][O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)=[CH:25][CH:26]=3)=[O:19])=[O:15])[CH2:10][CH2:11]2)[CH2:2][O:3][O:4]1

Participants

3

Reactant 2

HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamideHCID 86659468HCID 86659468, compound

Product 1

HCID 86659467HCID 86659467, compoundYield 48.1%

Procedure

Proceeding as in Example 1, but substituting 2-(2,3-dioxa-8-azaspiro[4.5]decan-8-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 219, (2S)-2-(2-(2,3-dioxa-8-azaspiro[4.5]decan-8-yl)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide (21.7 mg, 48.1%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.21 (s, 1H), 8.00 (d, 1H), 7.60 (d, 2H), 7.27-7.33 (m, 5H), 7.20-7.23 (m, 2H), 6.98-7.04 (m, 4H), 4.68-4.70 (m, 1H), 4.52 (s, 2H), 3.88 (s, 4H), 3.69-3.79 (m, 2H), 3.00 (s, 2H), 2.51-2.54 (m, 4H), 2.63-2.65 (m, 4H). MS (EI) for C31H34FN3O6. found 564.6 (MH+).

Sources & evidence

ORD record
ord-4ada7363450948068ec38ced1b10c68a
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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