Methanol → HCID 178516254, compound

HRID 2103689Notes

Reaction equation

HRID 2103689 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)[CH2:10]3)[S:8][C:4]=2[CH:3]=1.BrC1C=CC2[N:26]=[C:27]([C@H:29]3C[C@H:31]([N:33]4CCC[C@H]4C)[CH2:30]3)SC=2C=1.[OH-:41].[NH4+].CO>ClCCl>[N:13]1([C@H:11]2[CH2:12][C@H:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([N:33]5[C:31](=[O:41])[CH:30]=[CH:29][CH:27]=[N:26]5)[CH:20]=[CH:19][C:5]=4[N:6]=3)[CH2:10]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 178419317HCID 178419317, compoundHCID 178461421HCID 178461421, compound

Product 1

HCID 178516254HCID 178516254, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 22, substituting the product of Example 44A for the product of Example 1E. In this preparation, two isomeric products were obtained which represented the cis- and trans-configurations of the cyclobutane ring. The product that had a RF of 0.28 on TLC (TLC conditions 0.5% ammonium hydroxide and 5% methanol in dichloromethane on silica gel) was separated and purified by column chromatography on silica gel, eluting with 0.5% ammonium hydroxide and 5% methanol in dichloromethane to give an off-white solid, which corresponded to the trans isomer: mp 139-140° C. 1H NMR (500 MHz, CDCl3) δ ppm 8.15 (d, J=2.14 Hz, 1H) 8.05 (d, J=8.85 Hz, 1H) 7.93 (dd, J=3.81, 1.68 Hz, 1H) 7.70 (dd, J=8.85, 2.14 Hz, 1H) 7.24-7.31 (m, 1H) 7.09 (dd, J=9.46, 1.83 Hz, 1H) 3.80-3.92 (m, 1H) 3.10-3.19 (m, 1H) 2.53-2.70 (m, 4H) 2.21-2.47 (m, 4H) 1.58-1.72 (m, 4H) 1.42-1.55 (m, 2H). MS: (M+H)+=367.

Workup

  1. customIn this preparation, two isomeric products
  2. customwere obtained which
  3. customwas separated
  4. custompurified by column chromatography on silica gel
  5. washeluting with 0.5% ammonium hydroxide and 5% methanol in dichloromethane
  6. customto give an off-white solid, which

Sources & evidence

ORD record
ord-845da157de0a40c3932958aed34a022c
Source dataset
uspto-grants-2009_08
Patent number
US07576110B2

Reaction notes

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