Tetrahydrofuran → HCID 44213981, compound

HRID 1856856Notes

Reaction equation

HRID 1856856 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11][N:12]2[C:16]([C:17]([O:19]CC)=[O:18])=[C:15]([S:22][CH:23]3[CH2:28][CH2:27][C:26](=[CH:29][C:30]([O:32]CC)=[O:31])[CH2:25][CH2:24]3)[N:14]=[C:13]2[CH2:35][CH2:36][CH3:37])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.O1CCCC1>C(O)C>[C:30]([CH:29]=[C:26]1[CH2:25][CH2:24][CH:23]([S:22][C:15]2[N:14]=[C:13]([CH2:35][CH2:36][CH3:37])[N:12]([CH2:11][C:3]3[C:2]([Cl:1])=[CH:10][C:6]4[O:7][CH2:8][O:9][C:5]=4[CH:4]=3)[C:16]=2[C:17]([OH:19])=[O:18])[CH2:28][CH2:27]1)([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 54469756HCID 54469756, compound

Product 1

HCID 44213981HCID 44213981, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

880 mg of the product of Example 9 is introduced into 20 ml of tetrahydrofuran, 50 ml of ethanol and 25 ml of 2N soda are added and the reaction medium is left for 24 hours at ambient temperature. The tetrahydrofuran and the ethanol are evaporated off, then the reaction medium is acidified to pH 1. Extraction is carried out with ethyl acetate, followed by evaporation to dryness and the residue is recrystallized from ethyl acetate. In this way 490 mg of expected product is obtained. M.p.=168° C.

Workup

  1. additionare added
  2. customThe tetrahydrofuran and the ethanol are evaporated off
  3. extractionExtraction
  4. customfollowed by evaporation to dryness
  5. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ec9798d8881f40d2b33cbf742e649dfe
Source dataset
uspto-grants-2000_11
Patent number
US06143774

Reaction notes

Loading…