Acetyl chloride → HCID 22632478, compound

HRID 2417517Notes

Reaction equation

HRID 2417517 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][C:17](C(O)=O)=[CH:18][C:12]=3[N:11]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]4[CH2:35][CH:34]=[CH:33][CH2:32]4)=[O:30])=[CH:25][CH:24]=3)[C:10](=[O:36])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[CH2:56]([N:58](CC)CC)[CH3:57].C(Cl)(=O)C>C(O)(C)(C)C.Cl.O1CCOCC1.ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][C:17]([NH:58][C:56](=[O:46])[CH3:57])=[CH:18][C:12]=3[N:11]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]([N:31]4[CH2:35][CH:34]=[CH:33][CH2:32]4)=[O:30])=[CH:27][CH:28]=3)[C:10](=[O:36])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

10

Reactant 4

HCID 6367Acetyl chlorideHCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 22632627HCID 22632627, compound

Product 1

HCID 22632478HCID 22632478, compound

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

90 mg (0.17 mmol) of 4-(4-chlorobenzoyl)-2-oxo-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-2,3,4,5-tetrahydro-1H-benzo[e][1,4]-diazepine-8-carboxylic acid was dissolved in 5 ml of t-butyl alcohol. 58 mg (0.21 mmol) of diphenylphosphoryl azide and 0.056 ml (0.30 mmol) of triethylamine were added to the obtained solution and they were stirred at 70° C. overnight. The crude product obtained by the treatment with ethyl acetate as the extracting solvent was dissolved in 5 ml of 4N solution of hydrogen chloride in dioxane and the obtained solution was stirred at room temperature for 2 hours. The solvent was evaporated and the obtained crude product was dissolved in 5 ml of dichloromethane. 0.056 ml (0.30 mmol) of triethylamine and 0.028 ml of acetyl chloride were added to the obtained solution, and they were stirred at room temperature overnight. The solvent was evaporated and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Workup

  1. stirringthe obtained solution was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated
  3. customthe obtained crude product
  4. stirringwere stirred at room temperature overnight
  5. customThe solvent was evaporated
  6. customthe obtained crude product
  7. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-002116858bb348879353a36c55c97d77
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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