1,2-Dichloroethane → cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate

HRID 425024Notes

Reaction equation

HRID 425024 reaction equation
C(Cl)CCl.[CH3:5][C:6]([O:9][C:10]([NH:12][C@H:13]([C:17]([OH:19])=[O:18])[CH2:14][CH:15]=[CH2:16])=[O:11])([CH3:8])[CH3:7].[CH:20]1(O)[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:6]([O:9][C:10]([NH:12][C@@H:13]([CH2:14][CH:15]=[CH2:16])[C:17]([O:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:18])=[O:11])([CH3:5])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 2734487(2S)-2-(((tert-butoxy)carbonyl)amino)pent-4-enoic acid

Product 1

HCID 58150165cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoateYield 68.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of DMAP (0.057 g, 0.465 mmol) in DCM (20 ml) was added EDC (0.980 g, 5.11 mmol). A solution of Boc-L-allylglycine (1.0 g, 4.65 mmol) in DCM (5 ml) was added and the mixture stirred for 20 minutes at RT. Cyclopentanol (0.506 ml, 5.58 mmol) was then added and the mixture stirred overnight at RT for complete reaction. After concentration of the reaction solvent in vacuo, the residue was subjected to column chromatography eluting with 6% EtOAc in hexanes. Yield=0.907 g, 3.20 mmol, 68.9% yield. m/z 284 [M+H]+.

Workup

  1. stirringthe mixture stirred overnight at RT for complete reaction
  2. washeluting with 6% EtOAc in hexanes

Sources & evidence

ORD record
ord-8590790181434f2494ad1806c81d8ba9
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

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