Ammonia → HCID 66834493, compound

HRID 61839Notes

Reaction equation

HRID 61839 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]3[C:32](=[O:33])[C:31]4[C:30]5[C:25](=[CH:26][C:27]([Br:34])=[CH:28][CH:29]=5)[NH:24][C:23]=4[C:22]([CH3:36])([CH3:35])[C:21]=3[CH:37]=2)[O:8][C@H:7]([O:38][CH3:39])[C@@H:6]1[O:40]C(=O)C)(=O)C.N>CO>[Br:34][C:27]1[CH:26]=[C:25]2[C:30]([C:31]3[C:32](=[O:33])[C:20]4[CH:19]=[CH:18][C:17]([O:16][CH2:15][C@@H:9]5[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([OH:40])[C@@H:7]([O:38][CH3:39])[O:8]5)=[CH:37][C:21]=4[C:22]([CH3:36])([CH3:35])[C:23]=3[NH:24]2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66834255HCID 66834255, compound

Product 1

HCID 66834493HCID 66834493, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under nitrogen atmosphere, to acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-(3-bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-8-yl oxymethyl)-2-methoxy-tetrahydro-pyran-3-yl ester (Compound T12-1, 34.0 mg, 51.63 μmol), methanol solution (2.50 mL, 2 M) of ammonia was added, and the mixture was stirred at room temperature for 21 hr. The reaction solution was concentrated under reduced pressure, and the resulting resides were washed with diethyl ether to obtain the target compound (25.7 mg, 94%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washthe resulting resides were washed with diethyl ether

Sources & evidence

ORD record
ord-908a898c3a90496fafbfd77bedd111c9
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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