Ethyl Acetate → HCID 86747888, compound

HRID 1034371Notes

Reaction equation

HRID 1034371 reaction equation
Cl.CN(C)CCCN=C=NCC.[OH:13][C:14]1[C:23]2[C@@H:22]3[CH2:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH2:27][C@H:21]3[C:20]([CH3:32])([CH3:31])[O:19][C:18]=2[CH:17]=[C:16]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:15]=1.O[N:39]1[C:43](=[O:44])[CH2:42][CH2:41][C:40]1=[O:45].CCOC(C)=O>C(Cl)Cl>[OH:13][C:14]1[C:23]2[C@@H:22]3[CH2:24][C:25]([C:28]([O:30][N:39]4[C:43](=[O:44])[CH2:42][CH2:41][C:40]4=[O:45])=[O:29])=[CH:26][CH2:27][C@H:21]3[C:20]([CH3:31])([CH3:32])[O:19][C:18]=2[CH:17]=[C:16]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 80170N-HydroxysuccinimideHCID 1623891-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-9-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86747888HCID 86747888, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an alternate approach, 2 equivalents of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC-HCl) as the coupling reagent in the reaction of (XI) were mixed with 1.5 equivalents of N-hydroxysuccinimide in CH2Cl2 at reflux for 24 h. Dilution of the resulting reaction mixture with EtOAc, washing with water, saturated NaHCO3, saturated NaCl, drying over Na2SO4 and evaporation in vacuo then gave a gum. This was subjected to chromatography on silica, eluting with EtOAc-hexanes (1:1) to give (XII) as an off-white foam, [α]D -208° (CHCl3), (M+H)+ (FAB) 442.2260 (Calc 442.2230).

Workup

  1. temperatureat reflux for 24 h
  2. washwashing with water, saturated NaHCO3, saturated NaCl
  3. dry with materialdrying over Na2SO4 and evaporation in vacuo
  4. customthen gave a gum
  5. washeluting with EtOAc-hexanes (1:1)

Sources & evidence

ORD record
ord-2a054a73a7e94eda9a1f05d122b4f5fa
Source dataset
uspto-grants-1994_05
Patent number
US05315015

Reaction notes

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