Tetrahydrofuran → HCID 9827093, compound

HRID 1856848Notes

Reaction equation

HRID 1856848 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][CH:26]([CH2:29][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]([CH2:29][CH: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 54260776HCID 54260776, compound

Product 1

HCID 9827093HCID 9827093, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

760 mg of the product of Example 1 is introduced into 20 ml of tetrahydrofuran, 50 ml of ethanol and 25 ml of 2N soda are added and the whole 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. After extraction with ethyl acetate and evaporating to dryness, the residue is recrystallized from ethanol. 490 mg of expected product is obtained. M.p.=166° C.

Workup

  1. additionare added
  2. customThe tetrahydrofuran and the ethanol are evaporated off
  3. extractionAfter extraction with ethyl acetate
  4. customevaporating to dryness
  5. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-5448facff2ff482ba6d10448bdf64274
Source dataset
uspto-grants-2000_11
Patent number
US06143774

Reaction notes

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