Hydrochloric Acid → HCID 10136284, compound

HRID 1829609Notes

Reaction equation

HRID 1829609 reaction equation
C(O[C:6]([N:8]1[C:20]2[C:11](=[C:12]3[C:17](=[C:18]([OH:21])[CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:10]([CH2:22][Cl:23])[CH2:9]1)=[O:7])(C)(C)C.Cl.[OH:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH:29]=[CH:30]C(O)=O.CCN=C=NCCCN(C)C>O1CCOCC1.CC(N(C)C)=O>[Cl:23][CH2:22][CH:10]1[C:11]2=[C:12]3[C:17](=[C:18]([OH:21])[CH:19]=[C:20]2[N:8]([C:6](=[O:7])/[CH:30]=[CH:29]/[C:28]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:26]([OH:25])[CH:27]=2)[CH2:9]1)[N:16]=[CH:15][CH:14]=[CH:13]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHCID 22053387HCID 22053387, compound

Product 1

HCID 10136284HCID 10136284, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Procedure

A suspension of 16 (0.10 g, 0.30 mmol) in dioxane (5 mL) was saturated with HCl, stirred at r.t. over 5 h and evaporated. 3-Hydroxy-4-methoxycinnamic acid (predominantly trans) (0.070 g, 0.36 mmol), EDCI (0.29 g, 1.50 mmol) and DMA (3 mL) were added to the remaining yellow solid, and the red mixture was stirred at r.t. for 3 h. The mixture was partitioned between CH2Cl2 and cold 5% KHCO3 solution. The aqueous layer was extracted with CH2Cl2 (×3). The CH2Cl2 extracts were dried (brine, Na2SO4). Flash chromatography (CH2Cl2/MeOH; 93:7) followed by recrystallisation (CH2Cl2/Et2O) gave 18f (0.01 g, 8%) as a yellow solid: mp 215–218° C.; 1H NMR [(CD3)2SO]δ 9.96 (bs, 1 H), 9.13 (s, 1 H), 8.73 (dd, J=4.1, 1.4, 1 H), 8.36 (dd, J=8.5, 1.4, 1 H), 8.17 (bs, 1 H), 7.57 (d, J=15.3, 1 H), 7.54 (dd, J=8.5, 4.1, 1 H), 7.25 (d, J=2.0, 1 H), 7.20 (dd, J=8.4, 2.0, 1 H), 6.99 (d, J=8.1, 1 H), 6.96 (d, J=15.0, 1 H), 4.54 (dd, J=10.5, 9.4, 1 H), 4.44 (dd, J=11.1, 2.6, 1 H), 4.00 (dd, J=11.2, 3.3, 1 H),3.88 (dd, J=11.1, 7.5, 1 H), 3.83 (s, 3H). C22H1935ClN2O4 requires M+H 411.1112. Found (FAB) 411.1127.

Workup

  1. customevaporated
  2. stirringthe red mixture was stirred at r.t. for 3 h
  3. customThe mixture was partitioned between CH2Cl2 and cold 5% KHCO3 solution
  4. extractionThe aqueous layer was extracted with CH2Cl2 (×3)
  5. dry with materialThe CH2Cl2 extracts were dried (brine, Na2SO4)
  6. customFlash chromatography (CH2Cl2/MeOH; 93:7) followed by recrystallisation (CH2Cl2/Et2O)

Sources & evidence

ORD record
ord-e8c9203fdd7d4bc1a498dddf12f4df10
Source dataset
uspto-grants-2006_06
Patent number
US07064117B2

Reaction notes

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