Ammonium Hydroxide → HCID 9959156, compound

HRID 395255Notes

Reaction equation

HRID 395255 reaction equation
[CH2:1]1[O:42][C:4]2=[CH:5][C:6]3[C:11]4[C:12]5[C:37](=[O:38])[N:36](CO)[C:35](=[O:41])[C:13]=5[C:14]5[C:15]6[C:20]([N:21]([C@@H:23]7[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]7[OH:25])[C:22]=5[C:10]=4[NH:9][C:7]=3[CH:8]=[C:3]2[O:2]1)=[CH:19][CH:18]=[C:17]([OH:34])[CH:16]=6.[NH4+].[OH-]>CO>[CH2:1]1[O:42][C:4]2=[CH:5][C:6]3[C:11]4[C:12]5[C:37](=[O:38])[NH:36][C:35](=[O:41])[C:13]=5[C:14]5[C:15]6[C:20]([N:21]([C@@H:23]7[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]7[OH:25])[C:22]=5[C:10]=4[NH:9][C:7]=3[CH:8]=[C:3]2[O:2]1)=[CH:19][CH:18]=[C:17]([OH:34])[CH:16]=6

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 69625554HCID 69625554, compound

Product 1

HCID 9959156HCID 9959156, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 16 (30.0 mg, 0.052 mmol) in MeOH (2.0 mL) was added NH4OH (4.0 mL). The mixture was stirred at ambient temperature for 3 hours, then concentrated in vacuo to give a crude solid. Flash silica gel column chromatography eluting with MeOH/AcOH/EtOAc (12/1/87) afforded 26.1 mg (91.1%) as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a crude solid
  3. washFlash silica gel column chromatography eluting with MeOH/AcOH/EtOAc (12/1/87)
  4. customafforded 26.1 mg (91.1%) as a yellow solid

Sources & evidence

ORD record
ord-f6b2c6faed4d4d7cb9104a3bfacb2cc8
Source dataset
uspto-grants-2003_08
Patent number
US06605596B2

Reaction notes

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