HCID 9858581, compound → HCID 9964334, compound

HRID 1369172Notes

Reaction equation

HRID 1369172 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C@H:9]([NH:14]C(=O)C3C=CC=CC=3CO)[C@H:10]2[OH:13])=[CH:6][CH:5]=1)[CH3:2].C(OC1C=C2C(C[C@H](NC(=O)C3C=CC=CC=3CO)[C@@H]2O)=CC=1)C>C(O)(=O)C>[NH2:14][C@H:9]1[CH2:8][C:7]2[C:11](=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)[C@@H:10]1[OH:13]

Participants

4

Reactant 2

HCID 9858581HCID 9858581, compoundHCID 9967158HCID 9967158, compound

Product 1

HCID 9964334HCID 9964334, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-[(1S,2S)-6-ethoxy-2,3-dihydro-1-hydroxy-1H-inden-2-yl]-2-(hydroxymethyl)benzamide and N-[(1R,2S)-6-ethoxy-2,3-dihydro-1-hydroxy-1H-inden-2-yl]-2-(hydroxymethyl)benzamide (XVII, Example 16, 200 mg, 0.61 mmol) is dissolved in acetic acid (2.5 mL). The reaction mixture is stirred for 18 hr at 80°. Then the mixture is partitioned between methylene chloride and water. The aqueous phase is separated and adjusted to pH=10 using aqueous ammonium. The product is extracted with methylene chloride. The organic layers are concentrated to give the same title compound (VII) as EXAMPLE 6 and its cis-diastereomer.

Workup

  1. customThen the mixture is partitioned between methylene chloride and water
  2. customThe aqueous phase is separated
  3. extractionThe product is extracted with methylene chloride
  4. concentrationThe organic layers are concentrated

Sources & evidence

ORD record
ord-7cf03f41abf144cf9b60c9ecb00e5871
Source dataset
uspto-grants-2003_06
Patent number
US06576769B2

Reaction notes

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