HCID 21193074, compound → HCID 20664070, compound

HRID 1068204Notes

Reaction equation

[CH3:1][CH:2]1[C@H:6]([CH:7]=O)[C@@H:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH2:4][N:3]1[C@H:16]([CH2:27][CH:28]1[CH2:30][CH2:29]1)[C:17]([O:19]CC1C=CC=CC=1)=[O:18].FC(F)(F)C(O)=O.[CH2:38]([C:45]1[CH:49]=[C:48]([CH:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[N:47]([CH2:56][CH3:57])[N:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH3:1][CH:2]1[C@H:6]([CH2:7][N:53]2[CH2:54][CH2:55][CH:50]([C:48]3[N:47]([CH2:56][CH3:57])[N:46]=[C:45]([CH2:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:49]=3)[CH2:51][CH2:52]2)[C@@H:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH2:4][N:3]1[C@H:16]([CH2:27][CH:28]1[CH2:29][CH2:30]1)[C:17]([OH:19])=[O:18]

Participants

Reactant 2

HCID 21193074HCID 21193074, compound

HCID 131722701HCID 131722701, compound

Product 1

HCID 20664070HCID 20664070, compoundYield 46.1%

Procedure

2-(R)-(2-Methyl-3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclopropyl)propionic acid, benzyl ester (54 mg, 0.13 mmol, from Step D) and 4-(3-benzyl-1-ethyl-(1H-pyrazol-5-yl))piperidine trifluoroacetate (58 mg, 0.17 mmol, from Example 1, Step C) were reacted via the procedure described in Example 1, Steps D and E to afford 34.3 mg (46% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ0.04-0.11 (m, 1H), 0.14-0.20 (m, 1H), 0.41-0.49 (m, 1H), 0.51-0.57 (m, 1H), 0.68-0.75 (m, 1H), 1.23 (t, 3H), 1.63 (d, 3H), 1.80-2.10 (m, 6H), 2.65-2.78 (m, 1H), 2.84-2.98 (m 2H), 3.00-3.10 (m, 2H), 3.16-3.23 (m, 1H), 3.30-3.40 (m, 1H), 3.50-3.68 (m, 4H), 4.02 (s, 2H), 4.15-4.20 (m, 1H), 4.20-4.30 (m, 3H), 5.24 (d, 1H), 5.39 (d, 1H), 5.93 (s, 1H), 7.02-7.44 (m, 14 H); ESI-MS (M+H): 663.9; HPLC A: 2.04 min.

Sources & evidence

ORD record: ord-6797f5a885cb466da8943aa38ceb51ea
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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