Formic Acid → HCID 21713902, compound

HRID 649815Notes

Reaction equation

HRID 649815 reaction equation
[CH:1]1([C:7]([N:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=3[O:25][CH3:26])[CH2:14][CH2:13]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:33](O)=[O:34]>C(OCC)(=O)C>[CH:1]1([C:7]([N:9]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][CH:33]=[O:34])=[CH:20][C:19]=3[O:25][CH3:26])[CH2:14][CH2:13]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 21713926HCID 21713926, compound

Product 1

HCID 21713902HCID 21713902, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 0.140 g of the compound of Example 6 and 0.4 mL of formic acid in 8 mL of ethyl acetate was stirred at room temperature for 8 h. Afterwards, the reaction mixture was diluted with 40 mL of ethyl acetate, washed with 1 N sodium hydroxide and water, dried on sodium sulphate and evaporated to dryness in vacuo. The crude was purified by flash chromatography (ethyl acetate—3N ammonia in methanol 95:5) to afford 0. 130 g (89%) of the title product.

Workup

  1. washwashed with 1 N sodium hydroxide and water
  2. customdried on sodium sulphate
  3. customevaporated to dryness in vacuo
  4. customThe crude was purified by flash chromatography (ethyl acetate—3N ammonia in methanol 95:5)
  5. customto afford 0

Sources & evidence

ORD record
ord-2ec22447c99e4b75b377010aaa5a59b8
Source dataset
uspto-grants-2001_08
Patent number
US06271234B1

Reaction notes

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