Dicyclohexylcarbodiimide → (2R)-4-(4-oxo-4-(tetrahydro-2H-pyran-2-yloxyamino)butyl)phenyl 3-(5-(benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoate

HRID 885711Notes

Reaction equation

HRID 885711 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([OH:19])=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][C:38]([NH:40][O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][O:43]2)=[O:39])=[CH:31][CH:30]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([O:19][C:29]2[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][CH2:37][C:38](=[O:39])[NH:40][O:41][C@@H:42]3[CH2:47][CH2:46][CH2:45][CH2:44][O:43]3)=[CH:33][CH:34]=2)=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 67001556(R)-3-(5-(Benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoic acidHCID 866595084-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86659509(2R)-4-(4-oxo-4-(tetrahydro-2H-pyran-2-yloxyamino)butyl)phenyl 3-(5-(benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(R)-3-(5-(Benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoic acid (0.19 g, 0.5 mmol), 4-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)-butanamide (0.14 g, 0.5 mmol), and DMAP (0.06 g, 0.5 mmol) were added into DCM (10 mL) and stirred at 0° C. for 10 min. A solution of DCC (0.12 g, 0.6 mmol) in DCM (5 mL) was added to the above-mentioned solution dropwise. The mixture was stirred from 0° C. at room temperature for 1 h (monitored by TLC). The white solid was removed and the filtrated was then evaporated in vacuo. Ethyl acetoacetate was added and the solid was again removed. The solution was evaporated in vacuo. The residue was purified by chromatography (EA:Hex=1:5) to give the title compound.

Workup

  1. stirringThe mixture was stirred from 0° C. at room temperature for 1 h (monitored by TLC)
  2. customThe white solid was removed
  3. customthe filtrated was then evaporated in vacuo
  4. additionEthyl acetoacetate was added
  5. customthe solid was again removed
  6. customThe solution was evaporated in vacuo
  7. customThe residue was purified by chromatography (EA:Hex=1:5)

Sources & evidence

ORD record
ord-7f74e26e32644d36818201dd646a826b
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

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