Ammonia → HCID 58124957, compound

HRID 1971762Notes

Reaction equation

HRID 1971762 reaction equation
[C:1]([N:5]1[CH2:40][CH2:39][CH2:38][CH2:37][C:8]2[C:9]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20]#[C:21][CH2:22][C@@H:23]5[CH2:27][O:26]C(C)(C)[O:24]5)[C:16]([O:30][CH3:31])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:41])([CH3:4])([CH3:3])[CH3:2].[OH2:42].N>C(O)(=O)C>[C:1]([N:5]1[CH2:40][CH2:39][CH2:38][CH2:37][C:8]2[C:9]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20](=[O:42])[CH2:21][CH2:22][C@@H:23]([OH:24])[CH2:27][OH:26])[C:16]([O:30][CH3:31])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:41])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 58124806HCID 58124806, compound

Product 1

HCID 58124957HCID 58124957, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 40 mg of 28a in 1 mL 80% acetic acid was stirred at room temperature for 16 h. Then water was added and the mixture was made alkaline with ammonia. The mixture was extracted with 2×ethyl acetate. The combined organic phases were dried and concentrated. The crude product was purified by preparative HPLC on a reversed phase C18 column to give 8.8 mg of compound 28b.

Workup

  1. extractionThe mixture was extracted with 2×ethyl acetate
  2. customThe combined organic phases were dried
  3. concentrationconcentrated
  4. customThe crude product was purified by preparative HPLC on a reversed phase C18 column

Sources & evidence

ORD record
ord-b189bedd02e946b0980868dbca828f5f
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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