1215322-31-8 → HCID 45376499, compound

HRID 1630145Notes

Reaction equation

HRID 1630145 reaction equation
Cl.[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH2:11][C:12]([OH:14])=O.[NH2:15][C@@H:16]([CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[O:18]>>[CH2:36]([O:35][CH2:34][C@H:16]([NH:15][C:12](=[O:14])[CH2:11][N:3]1[CH2:2][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)=[O:18])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 470006061215322-31-8HCID 67009137(S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide

Product 1

HCID 45376499HCID 45376499, compoundYield 27.1%

Procedure

Proceeding as in Example 1, but substituting 2-(isoindolin-2-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 240, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(isoindolin-2-yl)acetamido)propanamide (11.7 g, 27.1%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.23 (s, 1H), 8.08 (d, 1H), 7.60 (d, 2H), 7.26 (m, 5H), 7.22 (m, 6H), 7.04-6.98 (m, 4H), 4.75 (m, 1H), 4.52 (s, 2H), 4.00 (s, 4H), 3.73 (m, 2H), 3.42 (s, 2H). MS (EI) for C32H30FN3O4. found 540.6 (MH+).

Sources & evidence

ORD record
ord-4da9ae83c5a4402cb930e13d3f294ad3
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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