4-(2-phenoxyethoxy)benzoic acid → HCID 67619421, compound

HRID 2293417Notes

Reaction equation

[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O:25]([CH2:32][CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41](=[O:44])[CH2:42]Cl)=[CH:37][CH:36]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O(CCOC1C=CC(C(O)=O)=CC=1)C1C=CC=CC=1>>[O:44]=[C:41]([C:38]1[CH:39]=[CH:40][C:35]([O:34][CH2:33][CH2:32][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:36][CH:37]=1)[CH2:42][N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([N:16]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5]

Participants

Reactant 3

HCID 2745474-(2-phenoxyethoxy)benzoic acid

HCID 53772281HCID 53772281, compound

HCID 86751513HCID 86751513, compound

Product 1

HCID 67619421HCID 67619421, compound

Procedure

Using the procedure described in Example 5, treatment of L-proline-L-isoleucine benzylamide (200 mg, 0.63 mmol) with 4'-phenoxyethoxy-2-chloroacetophenone, (275 mg, 0.95 mmol, 1.5 eq; prepared from 4-(2-phenoxyethoxy)benzoic acid by the method described in example 1), provided 80 mg of L-isoleucine, N-[1-{2-oxo-2-[4-(2-phenoxyethoxy)-phenyl]-ethyl}-L-prolyl] benzylamide as a crystalline solid.

Sources & evidence

ORD record: ord-4431cffce60841e6ba67b5133476e34d
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686424

Reaction notes

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