HCID 71245530, compound → HCID 71245548, compound

HRID 2369846Notes

Reaction equation

HRID 2369846 reaction equation
[F:1][C@@:2]12[C@:15]3([CH3:16])[C:10](=[CH:11][C:12](=[O:17])[CH:13]=[CH:14]3)[C@@H:9]([F:18])[CH2:8][C@H:7]1[C@@H:6]1[CH2:19][C@@H:20]3[C@:24]([C:25](=[O:31])[CH2:26][O:27]C(=O)C)([C@@:5]1([CH3:42])[CH2:4][C@@H:3]2[OH:43])[CH2:23][N:22]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1)[CH2:21]3>CO>[F:1][C@@:2]12[C@:15]3([CH3:16])[C:10](=[CH:11][C:12](=[O:17])[CH:13]=[CH:14]3)[C@@H:9]([F:18])[CH2:8][C@H:7]1[C@@H:6]1[CH2:19][C@@H:20]3[C@:24]([C:25](=[O:31])[CH2:26][OH:27])([C@@:5]1([CH3:42])[CH2:4][C@@H:3]2[OH:43])[CH2:23][N:22]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1)[CH2:21]3

Participants

3

Reactant 1

HCID 71245530HCID 71245530, compound

Product 1

HCID 71245548HCID 71245548, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 16 (171 mg, 0.290 mmol) in MeOH (4 ml) was degassed bubbling nitrogen at RT for 20 minutes. After cooling to 0° C. K2CO3 (12 mg, 0.0.87 mmol) was added, and the mixture was stirred for 1 hour. The mixture was partitioned between AcOEt and brine. The organic phase was separated, dried over Na2SO4 and concentrated. The crude was purified by preparative HPLC(CH3CN/H2O without CF3COOH) to give the title compound (45 mg, 28% yield).

Workup

  1. custombubbling nitrogen at RT for 20 minutes
  2. additionK2CO3 (12 mg, 0.0.87 mmol) was added
  3. customThe mixture was partitioned between AcOEt and brine
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude was purified by preparative HPLC(CH3CN/H2O without CF3COOH)

Sources & evidence

ORD record
ord-5722be5dc95849efb0b44c508ef0ef87
Source dataset
uspto-grants-2014_04
Patent number
US08710037B2

Reaction notes

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