2-Methylpentaldehyde → HCID 11570490, compound

HRID 1784248Notes

Reaction equation

HRID 1784248 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[NH2:34])[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.[CH3:37][CH:38]([CH2:41][CH2:42][CH3:43])[CH:39]=O>ClCCCl>[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:25][C:26](=[O:35])[C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[NH:34][CH2:37][CH:38]([CH3:39])[CH2:41][CH2:42][CH3:43])[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:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:11]=1.[Cl:33][C:31]1[CH:30]=[CH:29][C:28]([NH:34][CH2:37][CH:38]([CH3:39])[CH2:41][CH2:42][CH3:43])=[C:27]([CH:32]=1)[C:26]([NH: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:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:11]=1)[C:3]([OH:2])=[O:36])=[O:35]

Participants

5

Reactant 2

HCID 312452-MethylpentaldehydeHCID 68859581HCID 68859581, compound

Product 2

HCID 11570490HCID 11570490, compoundHCID 68862040HCID 68862040, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(2S)-[5-chloro-2-(2-methyl-pentylamino)-benzoylamino]-3-(2′-phenoxy-biphenyl-4-yl)-propionic acid methyl ester was prepared following procedure G using (2S)-(2-amino-5-chloro-benzoylamino)-3-(2′-phenoxy-biphenyl-4-yl)-propionicacid methyl ester (100 mg, 0.2 mmol) prepared in Example 10, 2-methyl-pentanal (30 mg, 0.25 mmol) in DCE (4 mL). Purification by flash chromatography (ethyl acetate/hexanes 1:3) gave the title compound as a thick liquid, which was hydrolyzed according to Procedure C yielding the title compound (85 mg). LC/MS (m/z): 571 (M+1)+.

Workup

  1. customPurification by flash chromatography (ethyl acetate/hexanes 1:3)

Sources & evidence

ORD record
ord-ec97117fb1d0405f83914c9d3b93bbb2
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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