Acetic Anhydride → HCID 66818857, compound

HRID 1024809Notes

Reaction equation

HRID 1024809 reaction equation
C(OC(=O)C)(=O)C.[C:8]([O:12][C:13](=[O:54])[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([C:21](=[O:53])[NH:22][C:23]2[CH:28]=[C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37](=[NH:40])[NH:38]O)=[CH:33][CH:32]=3)[CH:26]=[C:25]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][C:46]([C:49](=[NH:52])[NH:50]O)=[CH:45][CH:44]=3)[CH:24]=2)[CH2:17][CH2:16]1)([CH3:11])([CH3:10])[CH3:9]>C(O)(=O)C.[Zn]>[C:8]([O:12][C:13](=[O:54])[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([C:21](=[O:53])[NH:22][C:23]2[CH:24]=[C:25]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][C:46]([C:49](=[NH:50])[NH2:52])=[CH:45][CH:44]=3)[CH:26]=[C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:37](=[NH:38])[NH2:40])=[CH:35][CH:36]=3)[CH:28]=2)[CH2:17][CH2:16]1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178452754HCID 178452754, compound

Product 1

HCID 66818857HCID 66818857, compoundYield 136.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Acetic anhydride (0.36 ml, 3.72 mmol) was added to the solution of (4-{3,5-bis-[4-(N-hydroxycarbamimidoyl)-benzyloxy]-phenylcarbamoyl}-cyclohexyl)-carbamic acid tert-butyl ester (0.40 g, 0.62 mmol) in 10 ml of acetic acid and reaction mixture was stirred for 3 h. After completion of reaction, at RT zinc dust (0.4 g, 6.2 mmol) was added and resulting mixture was stirred over night. Recation mixture was filtered through celite and filterate was concentrated to dryness. Product was washed with cold diethyl ether and dried to afford 0.52 g of the required product. Percentage purity (LCMS): 100.0%, (M−1)=615.2-1.

Workup

  1. customAfter completion of reaction
  2. customresulting mixture
  3. stirringwas stirred over night
  4. filtrationRecation mixture was filtered through celite and filterate
  5. concentrationwas concentrated to dryness
  6. washProduct was washed with cold diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-44126ec8eed841749974d8fb8c48ef74
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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