Trichloroethanol → Fmoc-Ser(OtBu)-OTce

HRID 491279Notes

Reaction equation

HRID 491279 reaction equation
[NH:1]([C:12]([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[Cl:29][C:30]([Cl:34])([Cl:33])[CH2:31]O.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:1]([C:12]([O:14][CH2:15][CH:16]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C@H:2]([C:9]([O:11][CH2:31][C:30]([Cl:34])([Cl:33])[Cl:29])=[O:10])[CH2:3][O:4][C:5]([CH3:7])([CH3:6])[CH3:8]

Participants

6

Reactant 3

HCID 8259TrichloroethanolHCID 10868DicyclohexylcarbodiimideHCID 2724633N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylserine

Product 1

HCID 10907393Fmoc-Ser(OtBu)-OTceYield 100.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Fmoc-Ser(tBu)-OH (1 g, 2.6 mmol) was dissolved in CH2Cl2 (7 mL). DMAP (0.15 g, 1.3 mmol, 0.5 equiv) and 2,2,2-trichloroethanol (Tce) (0.3 mL, 3.1 mmol, 1.2 equiv) were first added, and then DCC (0.63 g, 3.1 mmol, 1.2 equiv) in CH2Cl2 (2.5 mL) was added under N2 atmosphere at 0° C. The reaction mixture was allowed to stir for 18 h at room temperature. The organic reaction was cooled to 0° C., filtered and the filtrate was concentrate in vacuo. The resulting crude was dissolved in EtOAc (7 mL) and washed with 10% aqueous citric acid (2×10 mL), saturated aqueous NaHCO3 (2×10 mL) and brine (2×10 mL), dried (MgSO4), and concentrated in vacuo to give Fmoc-Ser(OtBu)-OTce (1.34 g), which was used without further purification.

Workup

  1. customThe organic reaction
  2. temperaturewas cooled to 0° C.
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrate in vacuo
  5. dissolutionThe resulting crude was dissolved in EtOAc (7 mL)
  6. washwashed with 10% aqueous citric acid (2×10 mL), saturated aqueous NaHCO3 (2×10 mL) and brine (2×10 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d648848c5844a5194574b52805409c1
Source dataset
uspto-grants-2009_05
Patent number
US07531506B2

Reaction notes

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