Hydrochloric Acid → HCID 19841753, compound

HRID 1638274Notes

Reaction equation

HRID 1638274 reaction equation
[ClH:1].C(OC([NH:9][C:10]12[CH:17]3[CH:12]4[CH:13]5[CH:16]3[CH:15]1[CH:14]5[CH:11]24)=O)(C)(C)C>CO>[Cl-:1].[NH4+:9].[CH:10]12[CH:17]3[CH:12]4[CH:13]5[CH:16]3[CH:15]1[CH:14]5[CH:11]24

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19841754tert-Butyl pentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octan-1-ylcarbamate

Product 1

HCID 19841753HCID 19841753, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl gas was bubbled through a suspension of 4.0 g (18.3 millimoles) (tert-butoxycarbonyl)aminocubane in 200 ml of wet methanol at -30° C. until the solution became homogeneous. The methanol was removed in vacuo and 50 ml ether/acetone (4:1) was added to the residue. The solid (2.4 g, 85%) was collected by filtration and dried. The light tan solid was used without further purification. An NMR spectrum of the product dissolved in fully deuterated dimethyl sulfoxide had peaks assigned the following sigma values, compared to tetramethylsilane: 8.9 ppm (broad singlet, 3 hydrogens) and 4.3-3.8 (multiplet, 7 hydrogens).

Workup

  1. customThe methanol was removed in vacuo and 50 ml ether/acetone (4:1)
  2. additionwas added to the residue
  3. filtrationThe solid (2.4 g, 85%) was collected by filtration
  4. customdried
  5. customThe light tan solid was used without further purification
  6. dissolutionAn NMR spectrum of the product dissolved in fully deuterated dimethyl sulfoxide

Sources & evidence

ORD record
ord-d377f7c8c23a420baaee69468686d210
Source dataset
uspto-grants-1989_11
Patent number
US04878968

Reaction notes

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