Acetic Acid → HCID 131717915, compound

HRID 1975678Notes

Reaction equation

HRID 1975678 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[O:6][C:7]3[CH:30]=[CH:29][CH:28]=[CH:27][C:8]=3[CH2:9][N:10]([C:11](=[O:26])[CH2:12][NH:13][C:14](=[O:25])[CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)[C:4]=2[CH:3]=1.C(O)(=O)C.Cl>O1CCOCC1>[ClH:1].[NH2:17][CH2:16][CH2:15][C:14]([NH:13][CH2:12][C:11]([N:10]1[CH2:9][C:8]2[CH:27]=[CH:28][CH:29]=[CH:30][C:7]=2[O:6][C:5]2[CH:31]=[CH:32][C:2]([Cl:1])=[CH:3][C:4]1=2)=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 54284901HCID 54284901, compound

Product 1

HCID 131717915HCID 131717915, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl [3-[[2-(8-chloro-10,11-dihydrodibenz[b,f][1,4]-oxazepin-10-yl)-2-oxoethyl]amino]-3-oxopropyl]carbamate (8.1 grams), glacial acetic acid (50 mL), and 6.95M HCl in dioxane (27 mL) was stirred at room temperature for 20 minutes. The reaction was evaporated in vacuo, and the residue was co-evaporated in vacuo twice with ethanol (3A; 170 mL each time). The resulting foam was crystallized from ethyl acetate/ethanol and dried in vacuo at 56° C. The yield of the title compound was 5.79 grams (85%). Analysis calculated for C18H26ClN3O3S×HCl: C, 54.56; H, 4.83; N, 10.60; Cl, 17.89. Found: C, 54.30; H, 4.79; N, 10.49; Cl, 16.77. DSC: 216°-217° C.

Workup

  1. customThe reaction was evaporated in vacuo
  2. customThe resulting foam was crystallized from ethyl acetate/ethanol
  3. customdried in vacuo at 56° C
  4. custom216°-217° C.

Sources & evidence

ORD record
ord-2f74c7f083694dfc8f9e195275f4b547
Source dataset
uspto-grants-1994_02
Patent number
US05288719

Reaction notes

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