Water → HCID 57994310, compound

HRID 1009966Notes

Reaction equation

HRID 1009966 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][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])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]1(O)[CH2:32][CH2:31][CH2:30][CH2:29]1.CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH:28]1([O:18][C:17](=[O:19])[C@@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 962WaterHCID 7298CyclopentanolHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57994310HCID 57994310, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid (10 g, 26.9 mmol) in DMF (100 ml) was added cyclopentanol (4.6 g, 53.8 mmol) and DMAP (329 mg, 2.69 mmol). The solution was cooled down to 0° C. and EDC.HCl (5.4 g, 28.2 mmol) was added. The reaction mixture was then stirred at r.t. for 22 hours. Water (100 ml) and EtOAc (100 ml) were added and the phases were separated. The aqueous phase was extracted with EtOAc (2×80 ml). The organics were washed with water (3×50 ml) and brine (50 ml), then dried over magnesium sulfate, filtered and evaporated in vacuo. The crude product was purified on column (Heptane/EtOAc 7:3) to yield the title compound (8.09 g, 68.4%). LCMS purity 96.6%, m/z 462 [M++Na]+.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (2×80 ml)
  3. washThe organics were washed with water (3×50 ml) and brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified on column (Heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-1bd2afa77e884ecb98ccb7d85f640d13
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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