1-Butanol → butyl (S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propionate

HRID 271864Notes

Reaction equation

HRID 271864 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH3:4].N=C=N.[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C@@H:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([N:41]([CH3:52])[C:42]([NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:43])[CH:36]=2)=[CH:31][CH:30]=1)[C:25]([OH:27])=[O:26])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C@@H:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([N:41]([CH3:52])[C:42]([NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:43])[CH:36]=2)=[CH:31][CH:30]=1)[C:25]([O:27][CH2:1][CH2:2][CH2:3][CH3:4])=[O:26])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 160435CarbodiimideHCID 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acid

Product 1

HCID 11764815butyl (S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propionateYield 20.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4.7 mg (63.3 μmol) of n-butanol, 5.7 mg (8.5 μmol) of PS-DMAP resin and 68 mg (94.0 μmol) of PS-carbodiimide are added successively to a solution containing 25 mg (42.3 μmol) of (S)-2-(2-benzoylphenylamino)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propionic acid (Example 2) in 0.6 ml of DCM. After stirring for 16 h at ambient temperature and then 5 h at 40° C., the reaction medium is filtered and the solvents are evaporated off. The reaction crude is purified by chromatography on a column of silica and eluted with a heptane/ethyl acetate mixture. 5.5 mg of butyl (S)-2-(2-benzoylphenylamino)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propionate are obtained with a 20% yield.

Workup

  1. filtration5 h at 40° C., the reaction medium is filtered
  2. customthe solvents are evaporated off
  3. customThe reaction crude
  4. customis purified by chromatography on a column of silica
  5. washeluted with a heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c15dc68fa7f84f62bd72948ac153bfea
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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