Potassium Carbonate → HCID 89814458, compound

HRID 1496802Notes

Reaction equation

HRID 1496802 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[C:18](=[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]2[C:13]([C:32]([OH:45])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:12]3)[C:8]1=[O:9])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].ClCC(OCC=[CH:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=O>CN(C)C=O>[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[C:18](=[C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]2[C:13]([C:32]([OH:45])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:12]3)[C:8]1=[O:9])=[O:5])[CH:2]=[CH:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 575458HCID 575458, compoundHCID 89814504HCID 89814504, compound

Product 1

HCID 89814458HCID 89814458, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A similar procedure (Hursthouse, M. B.; Khan, A.; Marson, C. M.; Porter, R. A. Tetrahedron Lett. 1995, 36, 33, 5979-5982) to that described for the preparation of 207 was followed using NRB (0.49 g, 1.0 mmol) and potassium carbonate (0.33 g, 2.4 mmol) in dimethylformamide (5 mL), and cinnamyl chloroacetate (0.3 g, 1.4 mmol) in dimethylformamide (2 mL), and the mixture stirred at room temperature for 2 h. Purification by flash chromatography (hexane/ethyl acetate 3:2) afforded 371 as a white solid (0.63 g, 0.9 mmol, 90%). 1H NMR (400 MHz, CDCl3) δ 3.40-4.55 (8H, m, CH2CH═CH, NCH2, H-1, H-2, H-3, H-4), 5.48 (0.5H, s, OH), 5.52 (0.3H, m, V/H-6), 5.53 (0.5H, s, OH), 5.55 (0.4H, m, Y/H-6), 6.03 (0.1H, m, U/H-6), 6.05 (0.2H, m, W/H-6), 6.21-6.29 (1H, m, CH2CH═CH), 6.60-7.60 (22H, m, CH2CH═CH, Ar), 8.40-8.60 (2H, m, αPyr).

Workup

  1. customPurification by flash chromatography (hexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-e572299a810a4bf78844df24f5934afd
Source dataset
uspto-grants-2015_12
Patent number
US09198420B2

Reaction notes

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