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

HRID 425029Notes

Reaction equation

HRID 425029 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][C:11]#[CH:12])=[O:7])([CH3:4])[CH3:3].[CH:16]1(O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][C:11]#[CH:12])[C:13]([O:15][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:14])=[O:7])([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 2734488(2S)-2-{[(tert-butoxy)carbonyl]amino}pent-4-ynoic acid

Product 1

HCID 59243606cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoateYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-L-propargyl glycine (5 g, 23.45 mmol) in DCM (100 ml) was added cyclopentanol (3.03 g, 35.2 mmol), EDC (4.93 g, 25.8 mmol) and DMAP (0.286 g, 2.345 mmol). The mixture was stirred overnight at RT. The solvent was removed under reduced pressure and the residue was subjected to column chromatography eluting with 7 to 12% EtOAc in hexanes. Yield=5.5 g, 19.55 mmol, 83% yield.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washeluting with 7 to 12% EtOAc in hexanes

Sources & evidence

ORD record
ord-08b3bbf783e44372bbe0a66aadeaf06a
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

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