Succinic anhydride → HCID 131732741, compound

HRID 1471362Notes

Reaction equation

HRID 1471362 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:58]2[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=2)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[O:10][CH2:11][CH2:12][CH:13]([OH:51])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C@H:24]2[CH2:48][CH2:47][C@@:46]3([CH3:49])[C:26](=[CH:27][CH2:28][C@@H:29]4[C@@H:45]3[CH2:44][CH2:43][C@@:42]3([CH3:50])[C@H:30]4[CH2:31][CH2:32][C@@H:33]3[C@H:34]([CH3:41])[CH2:35][CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:25]2)=[CH:5][CH:4]=1.[C:66]1(=[O:72])[O:71][C:69](=[O:70])[CH2:68][CH2:67]1.CCOC(C)=O>C(Cl)Cl>[CH3:65][O:64][C:61]1[CH:60]=[CH:59][C:58]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[O:10][CH2:11][CH2:12][CH:13]([O:51][C:66](=[O:72])[CH2:67][CH2:68][C:69]([OH:71])=[O:70])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C@H:24]2[CH2:48][CH2:47][C@@:46]3([CH3:49])[C:26](=[CH:27][CH2:28][C@@H:29]4[C@@H:45]3[CH2:44][CH2:43][C@@:42]3([CH3:50])[C@H:30]4[CH2:31][CH2:32][C@@H:33]3[C@H:34]([CH3:41])[CH2:35][CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:25]2)=[CH:63][CH:62]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8857Ethyl AcetateHCID 131732742HCID 131732742, compound

Product 1

HCID 131732741HCID 131732741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 20 mL scintillation vial was 1-((bis(4-methoxyphenyl)(phenyl)methoxy))-12-(Cholest-5-en-3β-oxy)dodecan-3-ol (0.5 g, 0.562 mmol) and succinic anhydride (0.113 g, 1.124 mmol) in DCM (10 ml) to give a colorless solution. TEA (0.313 ml, 2.249 mmol) was added and the mixture set to stir for 17 hours. The reaction was judged complete by TLC (25% EtOAc/Hex, PMA visualization). The reaction mixture was washed with 5% NaHPO4 solution (3×15 mL) and brine (1×15 mL). The organic phase was dried over sodium sulfate, filtered and concentrated to dryness for use without further purification. 1H NMR (300 MHz, CDCl3) δ0.70 (3H, s); 0.83-1.74 (49H, m); 1.77-2.12 (5H, m); 2.14-2.29 (1H, m); 2.33-2.44 (1H, m); 2.53-2.72 (4H, m); 3.00-3.09 (2H, m); 3.16 (1H, tt, J=11.2, 4.4 Hz); 3.48 (2H, t, J=6.8 Hz); 3.80 (6H, s); 4.85-5.00 (1H, m); 5.36 (1H, d, J=5.1 Hz); 6.78-6.90 (4H, m), 7.15-7.38 (7H, m); 7.40-7.49 (2H, m); 9.29 (1H, bs).

Workup

  1. customto give a colorless solution
  2. washThe reaction mixture was washed with 5% NaHPO4 solution (3×15 mL) and brine (1×15 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness for use without further purification

Sources & evidence

ORD record
ord-87afbabd1fde437d9ea50f592b901b9c
Source dataset
uspto-grants-2015_04
Patent number
US09012225B2

Reaction notes

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