HCID 67404573, compound → HCID 58005156, compound

HRID 1879266Notes

Reaction equation

HRID 1879266 reaction equation
Cl.[NH2:2][C@@H:3]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:4]([N:6]1[CH2:14][C@H:13]([O:15][CH2:16][C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[CH2:30])[CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH2:12][C@H:7]1[C:8]([O:10][CH3:11])=[O:9])=[O:5]>ClCCCl.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:31]1([C@H:3]([NH:2][CH2:20][CH2:19][CH2:18][CH2:17][CH:22]=[CH2:21])[C:4]([N:6]2[CH2:14][C@H:13]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[CH2:30])[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:12][C@H:7]2[C:8]([O:10][CH3:11])=[O:9])=[O:5])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

5

Reactant 1

HCID 67404573HCID 67404573, compound

Product 1

HCID 58005156HCID 58005156, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Et3N (2.0 eq.), hex-5-enal (1.0 eq.) (obtained from hex-5-en-1-ol via a PCC oxidation and sodium triacetoxyborohydride (1.3 eq.) were sequentially added to a 0.07 M solution of methyl (4R)-1-[(2S)-2-amino-2-cyclohexylacetyl]-4-[(3′-vinylbiphenyl-3-yl)methoxy]-L-prolinate hydrochloride 108 in DCE. The reaction mixture was stirred at RT for 2 h then it was diluted with DCM, saturated aqueous NaHCO3 and extracted. The collected organic layers were washed with brine, dried (Na2SO4) and evaporated under reduced pressure to yield a residue that was purified by flash chromatography (SiO2, PE:EtOAc=7:3) to afford the title compound 109 (67%) as a colourless oil.

Workup

  1. extractionextracted
  2. washThe collected organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto yield a residue that
  6. customwas purified by flash chromatography (SiO2, PE:EtOAc=7:3)

Sources & evidence

ORD record
ord-6bbfaaab7f9d4a8fa4f6dc448e3d5758
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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