Potassium Carbonate → HCID 131734194, compound

HRID 1496801Notes

Reaction equation

HRID 1496801 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(O[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62]CC)=O>CN(C)C=O>[OH:45][C:32]([C:13]1[CH:14]2[C:18](=[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]([CH:12]=1)[CH:10]1[C:8]([N:7]([CH2:6][C:4]([O:3][CH2:1][CH2:2][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[O:5])[C:16](=[O:17])[CH:15]21)=[O:9])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 228762Octyl chloroacetateHCID 89814504HCID 89814504, compound

Product 1

HCID 131734194HCID 131734194, compoundYield 71%

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 (0.37 g, 0.7 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in dimethylformamide (5 mL), and octyl chloroacetate (0.32 g, 1.5 mmol) in dimethylformamide (2 mL), and the mixture stirred at room temperature for 2 h. Purification by flash chromatography (hexane/ethyl acetate 2:1) afforded 369 as a white solid (0.34 g, 0.5 mmol, 71%). 1H NMR (400 MHz, CDCl3) δ 0.87-0.90 (3H, m, O(CH2)7CH3), 1.26-1.30 (10H, m, OCH2CH2(CH2)5CH3), 1.61-1.63 (2H, m, OCH2CH2(CH2)5CH3), 3.40-4.56 (8H, m, OCH2(CH2)6CH3, 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), 6.02 (0.1H, m, U/H-6), 6.04 (0.2H, m, W/H-6), 6.70-7.60 (16H, m, Ar), 8.40-8.60 (2H, m, αPyr).

Workup

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

Sources & evidence

ORD record
ord-204ad2f8daa54cdabc97edd3d45c12ea
Source dataset
uspto-grants-2015_12
Patent number
US09198420B2

Reaction notes

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