1,2-Dichloroethane → HCID 53994349, compound

HRID 1656692Notes

Reaction equation

HRID 1656692 reaction equation
C[C:2]([O:5][C:6]([C@@H:8]([NH:14]C(OCC1C=CC=CC=1)=O)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])C.C1CCC(NC2CCCCC2)CC1.C1[O:40][CH:39]1CO.C(Cl)CCl.C(Cl)CCl.CN(C1C=CN=CC=1)C>ClCCl.CN(C1C=CN=CC=1)C>[CH2:2]([O:5][C:6](=[O:7])[C@H:8]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[NH2:14])[CH:4]1[O:40][CH2:39]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 11164GlycidolHCID 13474835HCID 13474835, compoundHCID 131718230HCID 131718230, compound

Product 1

HCID 53994349HCID 53994349, compoundYield 141.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1720 mg (3.38 mmol) of Z-Glu-OtBu DCHA in 17 mL of dichloromethane was cooled to 0° C. and treated with 0.448 mL (6.75 mmol, 2.0 equiv) of glycidol, 41.2 mg (0.338 mmol, 0.1 equiv) of DMAP and 970 mg (5.06 mmol, 1.5 equiv) of EDC according to the general procedure for EDC/DMAP esterification. Purification by flash chromatography (30×150 mm silica gel, 35% ethyl acetate/hexane) gave 971 mg (73%) of the title compound: 1H NMR (300 MHz, CD3OD) δ7.38-7.24 (m, 5H), 5.09 (s, 2H), 4.41 (dd, J=2.9, 12.4 Hz, 1H), 4.13-4.09 (overlapping dd, 1H), 3.91-3.84 (overlapping dd, 1H), 3.32-3.16 (m, 1H), 2.80-2.78 (overlapping t, 1H), 2.64-2.61 (overlapping dd, 1H), 2.47 (t, J=7.6 Hz, 2H), 2.20-2.08 (m, 1H), 1.97-1.84 (m, 1H), 1.45 (s, 9H); MS(FAB) 394 (M+1), 338, 294, 260.

Workup

  1. customPurification by flash chromatography (30×150 mm silica gel, 35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-34c37342faeb4a3e942f4e325ba8e293
Source dataset
uspto-grants-1993_10
Patent number
US05254682

Reaction notes

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