Acetic Anhydride → HCID 22556957, compound

HRID 983810Notes

Reaction equation

HRID 983810 reaction equation
C(OC(=O)C)(=O)C.[Cl:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]3[CH:19]=[C:20]([CH2:31][C:32]([OH:34])=[O:33])[CH:21]=[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:23]=3[OH:24])[NH:15]2)=[CH:11][C:10]=1[C:35](=[NH:38])[NH:36]O>C(O)(=O)C.[Pd]>[C:35]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[Cl:8])[NH:15][C:14]([C:18]1[CH:19]=[C:20]([CH2:31][C:32]([OH:34])=[O:33])[CH:21]=[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:23]=1[OH:24])=[CH:13]2)(=[NH:36])[NH2:38]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178513215HCID 178513215, compound

Product 1

HCID 22556957HCID 22556957, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Acetic anhydride (1.1 eq, 0.77 ml, in 7 ml of AcOH) was added drop wise to a stirring solution of 3 g of 18 in 34 ml of acetic acid at ambient temperature under N2 over several minutes. HPLC 15 minutes thereafter indicated formation of a hydrophobic product. A catalytic amount of Pd/C (10% w/w) was added to the reaction mixture and teh reaction vessel then was charged with H2 (atm.). The reaction mixture was agitated for about 1.5 h. The agitated reaction mixture was passed through a celite pad (rinsed with ACOH). The filtrate was diluted with ethyl acetate to yield a precipitate. The colid was isolated and dried in vacuo to yield 2.05 g of the crude amdidine.

Workup

  1. customHPLC 15 minutes
  2. additionthen was charged with H2 (atm.)
  3. customThe agitated reaction mixture
  4. washwas passed through a celite pad (rinsed with ACOH)
  5. additionThe filtrate was diluted with ethyl acetate
  6. customto yield a precipitate
  7. customThe colid was isolated
  8. customdried in vacuo
  9. customto yield 2.05 g of the crude amdidine

Sources & evidence

ORD record
ord-6a398d8ba28545f4a7d1e38ec95d5670
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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