Citric Acid → HCID 86589685, compound

HRID 2217630Notes

Reaction equation

HRID 2217630 reaction equation
N1([O:10][C:11](=O)[C:12]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH:36]4[S:40][C:39](=[O:41])[NH:38][C:37]4=[O:42])=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)=[CH:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=2)C2C=CC=CC=2N=N1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[CH3:20][C:18]1[CH:19]=[C:14]([CH:13]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH:36]4[S:40][C:39](=[O:41])[NH:38][C:37]4=[O:42])=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)[C:11]([N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)=[O:10])[CH:15]=[C:16]([CH3:21])[CH:17]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 8083MorpholineHCID 72556532HCID 72556532, compound

Product 1

HCID 86589685HCID 86589685, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 48 (116 mg, 0.2 mmol) in dichloromethane (5 mL) at room temperature was added morpholine (87 μL, 1 mmol). Solution became clear. After 10 min the mixture was treated with 10% citric acid (4 mL). The dichloromethane layer was dried (MgSO4) and directly loaded onto a column which was eluted with hexanes:ethyl acetate (2:3) to yield 50 (104 mg, 86%) as a white foam. 1H NMR (400 MHz, DMSO-d6): δ 12.10 (br s, 1H), 7.27 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.8 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.8 Hz, 2H), 6.85 (s, 1H), 6.72 (s, 2H), 6.61 (s, 1H), 4.91 (dd, J=8.8 and 4.4 Hz, 1H), 3.59 (bs, 8H), 3.37 (dd, J=14.0 and 4.4 Hz, 1H), 3.12 (dd, J=14.0 and 8.8 Hz, 1H), 2.13 (s, 6H).

Workup

  1. dry with materialThe dichloromethane layer was dried (MgSO4)
  2. washwas eluted with hexanes:ethyl acetate (2:3)

Sources & evidence

ORD record
ord-2ebac405d76e4e2295fae3977c65198d
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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