Water → HCID 59521774, compound

HRID 1162859Notes

Reaction equation

HRID 1162859 reaction equation
O.[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][C@H:28]([CH2:47][O:48]CC1C=CC(OC)=CC=1)[O:29][C:30](=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:25])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][C@H:28]([CH2:47][OH:48])[O:29][C:30](=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:25])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 60089183HCID 60089183, compound

Product 1

HCID 59521774HCID 59521774, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of CH2Cl2 (50 mL) and H2O (5 mL) under air was added the diacylglycerol [7] (3.12 g, 4.00 mmol). DDQ (1.81 g, 8.00 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was diluted with CH2Cl2 (50 mL) and washed with saturated NaHCO3 solution (20 mL), brine (20 mL) and dried over MgSO4. Flash chromatography eluting with 40-50% EtOAc in hexane gave the alcohol [8] (2.40 g, 3.62 mmol, 91%) as an off white solid: (Found: C, 70.7; H, 10.1; N, 2.1. C39H67O7N requires C, 70.7; H, 10.2; N, 2.1%); m.p. 56-58° C. [α]D20=−3.2 (c 1.02 in CHCl3); Rf=0.20 (30% EtOAc/hexane); γmax(CHCl3)/cm−1 3450, 2924, 2854, 1724, 1602, 1517, 1465, 1413, 1372, 1251, 1164; δH (400 MHz; CDCl3) 7.34-7.25 (5 H, m, Bn), 5.10-5.05 (3 H, m, CH2CHCH2, OCH2C6H5), 4.81 (1 H, bs, NH), 4.31 (1 H, dd, J 11.9, 4.4, CH2CHCH2), 4.20 (1 H, dd, J 11.9, 5.8, CH2CHCH2), 3.71 (2 H, d, J 5.8, CH2CHCH2), 3.16 (2 H, q, J 6.6, CH2NH), 2.32 (2 H, t, J 7.5, OCOCH2), 2.30 (2 H, t, J 7.8, OCOCH2), 1.63-1.59 (4 H, m, OCOCH2CH2, CH2CH2NH), 1.58-1.45 (2 H, m, CH2CH2CH2NH), 1.25 (36 H, bs, COC15H31, C11H22NH), 0.87 (3 H, t, J 6.6, CH2CH3); δC (63.5 MHz; CDCl3) 173.7, 173.4 (OCO), 156.4 (NHCO), 136.7, 128.5, 128.0, 112.6 (4×Bn), 72.1 (CH), 66.6, 62.1, 61.4 (3×CH2), 41.1 (NHCH2), 34.3, 34.1, 31.9, 30.0, 29.7, 29.6, 29.5, 29.3, 29.2, 29.1, 26.7, 24.9, 22.7 (12×CH2), 14.1 (CH3); m/z (CI) [Found (M+Na)+ 684.4828. C39H67O7NNa requires M, 684.4816].

Workup

  1. washwashed with saturated NaHCO3 solution (20 mL), brine (20 mL)
  2. dry with materialdried over MgSO4
  3. washFlash chromatography eluting with 40-50% EtOAc in hexane

Sources & evidence

ORD record
ord-3bb3552f88b2476bbbaf8c14f0028eea
Source dataset
uspto-grants-2010_10
Patent number
US07820803B2

Reaction notes

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