HCID 54370964, compound → HCID 54433340, compound

HRID 727027Notes

Reaction equation

HRID 727027 reaction equation
[Cl:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[CH:26][C:27]([Br:29])=[CH:28][C:4]=2[N:3]=1>N.CO>[Br:29][C:27]1[CH:26]=[CH:25][C:5]2[N:6]([C@@H:7]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]3[OH:9])[C:2]([Cl:1])=[N:3][C:4]=2[CH:28]=1

Participants

3

Reactant 1

HCID 54370964HCID 54370964, compound

Product 1

HCID 54433340HCID 54433340, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

A solution of 0.304 g (0.621 mmole) of 86 in 10 mL of NH3 /MeOH was stirred in a pressure bottle at room temperature for 5 h. The reaction mixture was evaporated and coevaporated with MeOH (3×, bath temperature <4° C.). The residue was recrystallized from MeOH to give 0.192 g (85%) of 87 as white crystals. MP 154°-155° C. MS (Cl) m/e 362.9735 (40%, MH+ 362.9747), 1H NMR (DMSO-d6): d 8.01 (d, 1, 7-H, J7-6 =8.5 Hz), 7.87 (d, 1, 4-H, J4-6 =2.0 Hz), 7.41 (dd, 1, 6-H), 5.89 (d, 1, 1'-H, J1'-2' =8.0 Hz), 5.51 (d, 1, 2'-OH, J2'-2'OH 6-5 Hz), 5.28 (d, 1, 3'-OH, J3'-3'OH =4 5 Hz), 5.25 (t, 1, 5'-OH, J5'-5'OH =5.0 Hz), 4.44 (m, 1, 2'-H, J2'-3' =5.5 Hz), 4.13 (m, 1, 3'-H, J3'-4' =2.5 Hz), 3.98 (m, 1, 4'-H, J4'-5' =J4'-5| =3.5 Hz), 3.68 (m, 2, 5'-H and 5"-H, J5'-5" =12.0 Hz). 13C NMR (DMSO-d6): d 142.81 (C3a), 141.23 (C2), 132.20 (C7a), 125.92 (C6), 121.32 (C4), 115.27 (C5), 114.89 (C7), 89.08 (C1'), 86.21 (C4), 71.47 (C2'), 69.73 (C3'), 61.22 (C5').

Workup

  1. customThe reaction mixture was evaporated
  2. customcoevaporated with MeOH (3×, bath temperature <4° C.)
  3. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-90e40cf3424345da8de35b6d0901ac31
Source dataset
uspto-grants-1998_01
Patent number
US05712255

Reaction notes

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