(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acid → HCID 11744123, compound

HRID 1392080Notes

Reaction equation

HRID 1392080 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][CH2:6][C@H:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([CH3:15])[C:3]1=[O:16].[F:17][C:18]1[CH:19]=[C:20]([CH2:25][C:26]([NH:28][C@H:29]([C:31](O)=[O:32])[CH3:30])=[O:27])[CH:21]=[C:22]([F:24])[CH:23]=1>>[F:17][C:18]1[CH:19]=[C:20]([CH2:25][C:26]([NH:28][C@H:29]([C:31]([NH:1][C@@H:2]2[CH2:8][CH2:7][CH2:6][C@H:5]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:4]([CH3:15])[C:3]2=[O:16])=[O:32])[CH3:30])=[O:27])[CH:21]=[C:22]([F:24])[CH:23]=1

Participants

3

Reactant 2

HCID 12135350(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoic acidHCID 58691181HCID 58691181, compound

Product 1

HCID 11744123HCID 11744123, compound

Procedure

Using a procedure similar to that described in example 3, except using (3R,7R)-3-amino-1-methyl-7-phenylazepan-2-one (3f) (60 mg) to couple with N-[(3,5-difluorophenyl)acetyl]-L-alanine (1e) (67 mg), the title compound was obtained as a white solid (100 mg, 84%). 1H NMR (300 MHz, CDCl3) δ 1.39 (d, 3H), 1.57 (m, 1H), 1.94 (m, 3H), 2.14 (m, 2H), 2.51 (s, 3H), 3.56 (s, 2H), 4.51-4.56 (m, 1H), 4.92-4.95 (m, 2H), 6.24 (bd, 1H), 6.70-6.75 (m, 1H), 6.83-6.85 (bd, 2H), 7.28-7.39 (m, 6H). MS APCI, m/z=444 (M+1). LC/MS 2.33 min., Method A.

Sources & evidence

ORD record
ord-75b0d6411b6d4eb8a33b620103ff5686
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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