Pyridine → HCID 68867993, compound

HRID 1984810Notes

Reaction equation

HRID 1984810 reaction equation
C[O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Br:33])[CH:30]=[CH:29][C:28]=1N)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:8][CH:7]=1.[CH:37]1([CH2:42][C:43](Cl)=[O:44])[CH2:41][CH2:40][CH2:39][CH2:38]1.[N:46]1C=CC=CC=1>C(Cl)Cl>[Br:33][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([CH:32]=1)[C:26]([N:25]([C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:10][CH:11]=1)[C:3]([OH:2])=[O:36])[NH:46][C:43](=[O:44])[CH2:42][CH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1)=[O:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3485182Cyclopentylacetyl chlorideHCID 68870114HCID 68870114, compound2×

Product 1

HCID 68867993HCID 68867993, compoundYield 519.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(2-Amino-5-bromo-benzoylamino)-3-(2′-phenoxy-biphenyl-4-yl)-propionic acid methyl ester (0.2 g, 0.04 mmlo) in 5 ml of DCM was reacted with cyclopentyl acetyl chloride (82.6 mg, 0.06 mmol) and pyridine (60 mg, 0.08 mmol) as described in general procedure K. The resulting ester was hydrolyzed according to the general procedure C to afford the title compound (0.2 g) as a white solid. LCMS: 642 (M+1)+.

Sources & evidence

ORD record
ord-762ea31fcb6a46fbbc68fad2e3fd2edf
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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